Yellow hue compound and aqueous ink for ink-jet recording system using the same

ABSTRACT

Aqueous ink for ink-jet recording which contains at least a water-insoluble coloring matter, water and a resin as main components and which takes the form of an emulsion, in which the coloring matter is at least one yellow hue coloring matter selected from the group consisting of a quinophthalone compound represented by the formula (1); 
                         
and a pyridone azo compound represented by the formula (2);
 
                         
The ink is ink for ink-jet recording having excellent light resistance and storage stability, and enables formation of a high quality image without blotting, and obtained recording image is excellent in water resistance as ink for ink-jet recording.

TECHNICAL FIELD

The present invention relates to ink for ink-jet recording which issuited for ink-jet recording system. More specifically, it relates to acompound suited for yellow hue coloring matter for aqueous ink forink-jet recording, and ink for ink-jet recording using the same.

BACKGROUND ART

Aqueous ink has been ordinarily used as ink for recording in ink-jetrecording system. Aqueous ink basically comprises a coloring matter,water and an organic solvent, and it contains water as a main solvent inconsideration of an odor and a safety to human bodies and surroundings.

Further, as a coloring matter, water-soluble dyes such as acid dyes,basic dyes, reactive dyes and direct dyes are generally used.

With respect to ink for ink-jet recording and a coloring matter, thefollowing various characteristics are required.

That is:

(1) Properties of ink, such as a viscosity, a surface tension, aspecific conductivity, a density and pH are appropriate.

(2) A long-term storage stability of ink is good.

(3) A dissolution stability of a dissolution component is so high thatclogging of a nozzle does not occur.

(4) A quick-drying property in a recording material is good.

(5) A recorded image is vivid, and light resistance and water resistanceare good.

However, a coloring matter and ink that satisfy all thesecharacteristics have not yet been provided.

Especially, in ordinary aqueous ink, water-soluble dyes are used.Accordingly, when water is spilled on a recorded image, a dye is eluted,and a recorded image is blotted therewith or disappeared. Thus, it ismuch problematic in a water resistance.

At present, various studies have been made upon focussing on theimprovement of the water resistance.

For example, a method in which an organic solvent or a resin is added toink using a pigment or an oil-soluble dye as a coloring matter oraqueous ink using a water-soluble dye has been studied. However, in caseof using a pigment, there were problems that a dispersion stability wasbad and a storage stability was poor, inducing clogging of a nozzle. Incase of using an oil-soluble dye, an organic solvent was used, posing aproblem of an environmental sanitation such as an odor, and ink blottingnotably occurred, decreasing qualities of an image. Moreover, even incase of using ink containing additives, there were problems that astorage stability was poor, clogging of a nozzle occurred, and ink wasnot jetted well because a viscosity of ink was increased.

Recently, Japanese Patent Laid-Open No. 340835/1994 describes ink usingan aqueous dispersion containing a polyester resin colored with a dye ora pigment as a disperse phase. However, a pigment still suffers fromthese problems. Since a dye is also poor in a compatibility with aresin, it also involves such problems that a precipitate appears in ink,a storage stability is poor and clogging of a nozzle occurs.

As stated above, the characteristics of ink used in the ink-jetrecording system in particular are greatly influenced by thecharacteristics intrinsic to the coloring matter. Thus, the discovery ofa coloring matter that satisfies these conditions is quite important.

An object of the present invention is to provide a coloring matter whichis excellent in solubility into an organic solvent, water resistance,light resistance and compatibility with a resin in particular.

Another object of the present invention is to provide aqueous yellow hueink for ink-jet recording using the same, which is excellent in waterresistance, light resistance and storage stability, and which is mostsuited for ink-jet recording system.

DISCLOSURE OF INVENTION

The present inventors have carried out an extensive investigation toachieve the above objects, and have found that a compound represented bythe formula (1) and a compound represented by the formula (2) are acoloring matter met the above objects and thus have accomplished thepresent invention.

That is, the present invention is as follows.

(1) Aqueous ink for ink-jet recording which contains at least awater-insoluble coloring matter, water and a resin as main componentsand takes the form of an emulsion, the coloring matter being at leastone yellow hue coloring matter selected from the group consisting of

a quinophthalone compound represented by the formula (1);

wherein

each of R₁ to R₃ independently, represents a hydrogen atom, anunsubstituted or substituted alkyl group, —CONR₄R₅, or —COOR₆ (in whicheach of R₄ to R₆ independently, represents a hydrogen atom, anunsubstituted or substituted alkyl group, or an unsubstituted orsubstituted aryl group), and all of R₁ to R₃ are not a hydrogen atom atthe same time, and

a pyridone azo compound represented by the formula (2);

wherein

each of R₇ to R₁₁ independently, represents a hydrogen atom, a halogenatom, an unsubstituted or substituted alkyl group, an aralkyl group, anunsubstituted or substituted alkoxy group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted aryloxy group, ahydroxyl group, —NR₁₄R₁₅ (in which R₁₄ and R₁₅ independently, representsa hydrogen atom, an unsubstituted or substituted alkyl group, an aralkylgroup), —COX₁ [in which X₁ represents an unsubstituted or substitutedalkoxy group, an unsubstituted or substituted aryloxy group, or —NR₁₆R₁₇(in which each of R₁₆ and R₁₇ independently, represents a hydrogen atom,an unsubstituted or substituted alkyl group, an aralkyl group, or anunsubstituted or substituted aryl group)], —COO(CH₂)_(n)—COX₂, —OCOX₃,or —NHCOX₄ (in which each of X₂ to X₄ independently, represents anunsubstituted or substituted alkyl group, an aralkyl group, anunsubstituted or substituted aryl group, an unsubstituted or substitutedalkoxy group, or an unsubstituted or substituted aryloxy group, and n isan integer of 1 to 3),

R₁₂ represents an unsubstituted or substituted alkyl group,

R₁₃ represents an unsubstituted or substituted alkyl group, an aralkylgroup, or an unsubstituted or substituted aryl group.

(2) The aqueous ink for ink-jet recording according to the above 1wherein the yellow hue coloring matter is a quinophthalone compoundrepresented by the formula (1);

wherein

each of R₁ to R₃ independently, represents a hydrogen atom, anunsubstituted or substituted alkyl group, —CONR₄R₁₅, or —COOR₆ (in whicheach of R₄ to R₆ independently, represents a hydrogen atom, anunsubstituted or substituted alkyl group, or an unsubstituted orsubstituted aryl group), and all of R₁ to R₃ are not a hydrogen atom atthe same time.

(3) The aqueous ink for ink-jet recording according to the above 2wherein R₂ and R₃ in the formula (1) are —CONR₄R₅ or —COOR₆ (in whicheach of R₄ to R₆ independently, represents a hydrogen atom, anunsubstituted or substituted alkyl group, or an unsubstituted orsubstituted aryl group).(4) The aqueous ink for inkjet recording according to the above 2wherein R₁ in the formula (1) is a hydrogen atom, or an unsubstituted orsubstituted alkyl group having 5 or less carbon atoms, and one of R₂ orR₃ is a hydrogen atom and the other is —CONR₄R₅ or —COOR₆ (in which eachof R₄ to R₆ independently, represents a hydrogen atom, an unsubstitutedor substituted alkyl group, or an unsubstituted or substituted arylgroup).(5) The aqueous ink for ink-jet recording according to the above 2wherein R₁ in the formula (1) is a hydrogen atom, or an unsubstituted orsubstituted alkyl group having 5 or less carbon atoms, R₂ is a hydrogenatom, and R₃ is —CONR₄R₅ (in which each of R₄ and R₅ independently,represents an unsubstituted or substituted alkyl group having 6 or morecarbon atoms, or an unsubstituted or substituted aryl group).(6) The aqueous ink for ink-jet recording according to the above 1wherein the yellow hue coloring matter is a pyridone azo compoundrepresented by the formula (2);

wherein

each of R₇ to R₁₁ independently, represents a hydrogen atom, a halogenatom, an unsubstituted or substituted alkyl group, an aralkyl group, anunsubstituted or substituted alkoxy group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted aryloxy group, ahydroxyl group, —NR₁₄R₁₅ (in which each of R₁₄ and R₁₅ independently,represents a hydrogen atom, an unsubstituted or substituted alkyl group,or an aralkyl group), —COX₁ [in which X₁ represents an unsubstituted orsubstituted alkoxy group, an unsubstituted or substituted aryloxy group,or —NR₁₆R₁₇ (in which each of R₁₆ and R₁₇ independently, represents ahydrogen atom, an unsubstituted or substituted alkyl group, an aralkylgroup, or an unsubstituted or substituted aryl group)],—COO(CH₂)_(n)—COX₂, —OCOX₃, or —NHCOX₄ (in which X₂ to X₄ represents anunsubstituted or substituted alkyl group, an aralkyl group, anunsubstituted or substituted aryl group, an unsubstituted or substitutedalkoxy group, or an unsubstituted or substituted aryloxy group, and n isan integer of 1 to 3),

R₁₂ represents an unsubstituted or substituted alkyl group,

R₁₃ represents an unsubstituted or substituted alkyl group, an aralkylgroup, or an unsubstituted or substituted aryl group.

(7) The aqueous ink for ink-jet recording according to the above 6wherein at least one of R₇ to R₉ in the formula (2) is —COX₁, and R₁₃ isan unsubstituted or substituted alkyl group.

(8) The aqueous ink for ink jet recording according to the above 7wherein the unsubstituted or substituted alkyl group represented by R₁₃in the formula (2) is a linear or branched alkyl group having 8 or morecarbon atoms, or —(CH₂)_(n)COR₁₈ having 8 or more carbon atoms [in whichR₁₈ represents an unsubstituted or substituted alkoxy group, anunsubstituted or substituted aryloxy group, or —NR₁₉R₂₀ (in which eachof R₁₉ and R₂₀ independently, represents a hydrogen atom, anunsubstituted or substituted alkyl group, an aralkyl group, or anunsubstituted or substituted aryl group), and n is an integer of 1 or2].(9) A quinophthalone compound represented by the formula (1);

wherein

R₁ represents a linear, branched or cyclic alkyl group having 2 or morecarbon atoms,

R₂ represents a hydrogen atom,

R₃ represents —CONR₄R₅ (in which each of R₄ and R₅ independently,represents a linear, branched or cyclic alkyl group having 6 or morecarbon atoms).

(10) The quinophthalone compound according to the above 9 wherein in theformula (1), R₁ is isopropyl group, R₂ is a hydrogen atom, R₃ is—CONR₄R₅ (in which each of R₄ and R₅ independently, represents a linearor branched alkyl group having 8 or more carbon atoms).(11) A pyridone azo compound represented by the formula (2);

wherein

each of R₇ to R₁₁ independently, represents a hydrogen atom, a halogenatom, an unsubstituted or substituted alkyl group, an aralkyl group, anunsubstituted or substituted alkoxy group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted aryloxy group, ahydroxyl group, —NR₁₄R₁₅ (in which each of R₁₄ and R₁₅ independently,represents a hydrogen atom, an unsubstituted or substituted alkyl group,or an aralkyl group), —COX₁ [in which X₁ represents an unsubstituted orsubstituted alkoxy group, an unsubstituted or substituted aryloxy group,or —NR₁₆R₁₇ (in which R₁₆ and R₁₇ independently, represents a hydrogenatom, an unsubstituted or substituted alkyl group, an aralkyl group, oran unsubstituted or substituted aryl group)], —COO(CH₂)_(n)—COX₂,—OCOX₃, or —NHCOX₄ (in which X₂ to X₄ represents an unsubstituted orsubstituted alkyl group, an aralkyl group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted alkoxy group, oran unsubstituted or substituted aryloxy group, and n is an integer of 1to 3),

R₁₂ represents an unsubstituted or substituted alkyl group,

R₁₃ represents an unsubstituted or substituted alkyl group, an aralkylgroup, or an unsubstituted or substituted aryl group.

(12) The pyridone azo compound according to the above 11 wherein in theformula (2), at least one of R₇ to R₁₁ is —COX₁, and R₁₃ is anunsubstituted or substituted alkyl group.

(13) The pyridone azo compound according to the above 12 wherein in theformula (2), at least one of R₇ to R₁₁ is —CONR₁₆R₁₇.

(14) A resin fine particle colored by at least one yellow hue coloringmatter selected from the group consisting of;

a quinophthalone compound represented by the formula (1);

wherein

each of R₁ to R₃ independently, represents a hydrogen atom, anunsubstituted or substituted alkyl group, —CONR₄R₅, or —COOR₆ (in whicheach of R₄ to R₆ independently, represents a hydrogen atom, anunsubstituted or substituted alkyl group, or an unsubstituted orsubstituted aryl group), and all of R₁ to R₃ are not a hydrogen atom atthe same time, and

a pyridone azo compound represented by the formula (2);

wherein

each of R₇ to R₁₁ independently, represents a hydrogen atom, a halogenatom, an unsubstituted or substituted alkyl group, an aralkyl group, anunsubstituted or substituted alkoxy group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted aryloxy group, ahydroxyl group, —NR₁₄R₁₅ (in which each of R₁₄ and R₁₅ independently,represents a hydrogen atom, an unsubstituted or substituted alkyl group,or an aralkyl group), —COX₁ [in which X₁ represents an unsubstituted orsubstituted alkoxy group, an unsubstituted or substituted aryloxy group,or —NR₁₆R₁₇ (in which each of R₁₆ and R₁₇ independently, represents ahydrogen atom, an unsubstituted or substituted alkyl group, an aralkylgroup, an unsubstituted or substituted aryl group)], —COO(CH₂)_(n)—COX₂,—OCOX₃, or —NHCOX₄ (in which X₂ to X₄ represents an unsubstituted orsubstituted alkyl group, an aralkyl group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted alkoxy group, oran unsubstituted or substituted aryloxy group, and n is an integer of 1to 3),

R₁₂ represents an unsubstituted or substituted alkyl group,

R₁₃ represents an unsubstituted or substituted alkyl group, an aralkylgroup, or an unsubstituted or substituted aryl group.

(15) A dispersion obtained by dispersing in a water medium the resinfine particles of the above 14.

The yellow hue coloring matter of the present invention is excellent inwater-resistance in particular and also excellent in light resistanceand compatibility with a resin. Thus, it is suited for the aqueous inkfor ink-jet recording. Further, the aqueous ink for ink-jet recording ofthe present invention, which is produced using the coloring matter isexcellent in light resistance and storage stability. Especially, when itis used as aqueous ink for ink-jet recording system, the ink compositioncomprising containing at least the water insoluble yellow hue coloringmatter of the present invention, water and a resin as main componentsand forming an emulsion can enable to form a high-quality image withoutblotting. And the recorded image has excellent water resistance.

Consequently, the present invention can provide the aqueous inkproviding high-quality image, the yellow hue coloring matter havingexcellent light-resistance and storage stability applicable to ink forink-jet recording, resin fine particles used the coloring matter, andthe dispersion dispersed the particles in water.

BEST MODE FOR CARRYING OUT THE INVENTION

The present invention relates to aqueous ink for ink-jet recordingforming emulsion comprising containing as main components at least awater-insoluble coloring matter, water and a resin, in which

1) a coloring matter which is insoluble is at least one yellow huecompound selected from the group consisting of the compound representedby the formula (1) and the compound represented by the formula (2),

2) resin fine particles colored with at least one yellow hue coloringmatter selected from the group consisting of the compound represented bythe formula (1) and the compound represented by the formula (2),

3) dispersions dispersed the resin fine particles in aqueous medium, andfurther,

4) aqueous ink for ink-jet recording which is an emulsion emulsified anddispersed the resin fine particles.

The coloring matter of the present invention, namely, the coloringmatter preferably used in aqueous ink for ink-jet recording of thepresent invention is at least one yellow hue coloring matter[hereinafter also referred to as “a coloring matter” or “a coloringmatter for ink jet recording”] selected from the group consisting of aquinophthalone compound represented by the formula (1) and a pyridoneazo compound represented by the formula (2).

In the quinophthalone compound represented by the formula (1), each ofR₁ to R₃ independently, represents a hydrogen atom, an unsubstituted orsubstituted alkyl group, —CONR₄R₅ or —COOR₆ (in which each of R₄ to R₆independently, represents a hydrogen atom, an unsubstituted orsubstituted alkyl group, or an unsubstituted or substituted aryl group),provided all of R₁ to R₃ are not hydrogen atoms at the same time.

In the formula (1), an unsubstituted or substituted alkyl group is notlimited in particular, and includes;

linear, branched or cyclic alkyl groups such as methyl group, ethylgroup, n-propyl group, isopropyl group, n-butyl group, isobutyl group,tert-butyl group, sec-butyl group, n-pentyl group, isopentyl group,tert-pentyl group, sec-pentyl group, cyclopentyl group, n-hexyl group,1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group,4-methylpentyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group,1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 1,1,2-trimethylpropylgroup, 1,2,2-trimethylpropyl group, 1-ethylbutyl group, 2-ethylbutylgroup, 1-ethyl-2-methylpropyl group, cyclohexyl group, methylcyclopentylgroup, n-heptyl group, 1-methylhexyl group, 2-methylhexyl group,3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group,1,1-dimethylpentyl group, 1,2-dimethylpentyl group, 1,3-dimethylpentylgroup, 1,4-dimethylpentyl group, 2,2-dimethylpentyl group,2,3-dimethylpentyl group, 2,4-dimethylpentyl group, 3,3-dimethylpentylgroup, 3,4-dimethylpentyl group, 1-ethylpentyl group, 2-ethylpentylgroup, 3-ethylpentyl group, 1,1,2-trimethylbutyl group,1,1,3-trimethylbutyl group, 1,2,3-trimethylbutyl group,1,2,2-trimethylbutyl group, 1,3,3-trimethylbutyl group,2,3,3-trimethylbutyl group, 1-ethyl-1-methylbutyl group,1-ethyl-2-methylbutyl group, 1-ethyl-3-methylbutyl group,2-ethyl-1-methylbutyl group, 2-ethyl-3-methylbutyl group,1-n-propylbutyl group, 1-iso-propylbutyl group,1-iso-propyl-2-methylpropyl group, methylcyclohexyl group, n-octylgroup, 1-methylheptyl group, 2-methylheptyl group, 3-methylheptyl group,4-methylheptyl group, 5-methylheptyl group, 6-methylheptyl group,1,1-dimethylhexyl group, 1,2-dimethylhexyl group, 1,3-dimethylhexylgroup, 1,4-dimethylhexyl group, 1,5-dimethylhexyl group,2,2-dimethylhexyl group, 2,3-dimethylhexyl group, 2,4-dimethylhexylgroup, 2,5-dimethylhexyl group, 3,3-dimethylhexyl group,3,4-dimethylhexyl group, 3,5-dimethylhexyl group, 4,4-dimethylhexylgroup, 4,5-dimethylhexyl group, 1-ethylhexyl group, 2-ethyl hexyl group,3-ethylhexyl group, 4-ethylhexyl group, 1-n-propylpentyl group,2-n-propylpentyl group, 1-iso-propylpentyl group, 2-iso-propylpentylgroup, 1-ethyl-1-methylpentyl group, 1-ethyl-2-methylpentyl group,1-ethyl-3-methylpentyl group, 1-ethyl-4-methylpentyl group,2-ethyl-1-methylpentyl group, 2-ethyl-2-methylpentyl group,2-ethyl-3-methylpentyl group, 2-ethyl-4-methylpentyl group,3-ethyl-1-methylpentyl group, 3-ethyl-2-methylpentyl group,3-ethyl-3-methylpentyl group, 3-ethyl-4-methylpentyl group,1,1,2-trimethylpentyl group, 1,1,3-trimethylpentyl group,1,1,4-trimethylpentyl group, 1,2,2-trimethylpentyl group,1,2,3-trimethylpentyl group, 1,2,4-trimethylpentyl group,1,3,4-trimethylpentyl group, 2,2,3-trimethylpentyl group,2,2,4-trimethylpentyl group, 2,3,4-trimethylpentyl group,1,3,3-trimethylpentyl group, 2,3,3-trimethylpentyl group,3,3,4-trimethylpentyl group, 1,4,4-trimethylpentyl group,2,4,4-trimethylpentyl group, 3,4,4-trimethylpentyl group, 1-n-butylbutylgroup, 1-iso-butylbutyl group, 1-sec-butylbutyl group, 1-tert-butylbutylgroup, 2-tert-butylbutyl group, 1-n-propyl-1-methylbutyl group,1-n-propyl-2-methylbutyl group, 1-n-propyl-3-methylbutyl group,1-iso-propyl-1-methylbutyl group, 1-iso-propyl-2-methylbutyl group,1-iso-propyl-3-methylbutyl group, 1,1-diethylbutyl group,1,2-diethylbutyl group, 1-ethyl-1,2-dimethylbutyl group,1-ethyl-1,3-dimethylbutyl group, 1-ethyl-2,3-dimethylbutyl group,2-ethyl-1,1-dimethylbutyl group, 2-ethyl-1,2-dimethylbutyl group,2-ethyl-1,3-dimethylbutyl group, 2-ethyl-2,3-dimethylbutyl group,1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group,1,4-dimethylcyclohexyl group, ethylcyclohexyl group, n-nonyl group,3,5,5-trimethylhexyl group and n-decyl group;

linear, branched or cyclic haloalkyl groups substituted by one or morehalogen atoms, such as fluoromethyl group, trifluoromethyl group,chloromethyl group, dichloromethyl group, trichloromethyl group,bromomethyl group, dibromomethyl group, tribromomethyl group,fluoroethyl group, chloroethyl group, bromoethyl group, trifluoroethylgroup, pentafluoroethyl group, tetrachloroethyl group andhexafluoroisopropyl group;

linear, branched or cyclic alkoxy alkyl groups such as methoxymethylgroup, ethoxymethyl group, propoxymethyl group, butoxymethyl group,pentoxymethyl group, hexyloxymethyl group, cyclohexyloxymethyl group,methoxyethyl group, ethoxyethyl group, propoxyethyl group, butoxyethylgroup, pentoxyethyl group, hexyloxyethyl group, cyclohexyloxyethylgroup, methoxyethyl group, methoxyethoxyethyl group, methoxypropylgroup, ethoxypropyl group, propoxypropyl group, butoxypropyl group,pentoxypropyl group, hexyloxypropyl group, cyclohexylpropyl group andmethoxyethoxypropyl group;

linear, branched or cycloalkylthioalkyl groups such as methylthiomethylgroup, ethylthiomethyl group, propylthiomethyl group, butylthiomethylgroup, pentylthiomethyl group, hexylthiomethyl group,cyclohexylthiomethyl group, methylthioethyl group, ethylthioethyl group,propylthioethyl group, butylthioethyl group, pentylthioethyl group,hexylthioethyl group, cyclohexylthioethyl group, methoxyethylthioethylgroup, methylthiopropyl group, ethylthiopropyl group, propylthiopropylgroup, butylthiopropyl group, pentylthiopropyl group, hexylthiopropylgroup, cyclohexylthiopropyl group and methoxyethylthiopropyl group;

alkylaminoalkyl groups or dialkylaminoalkyl groups such asN-methylaminomethyl group, N,N-dimethylaminomethyl group,N-ethlaminomethyl group, N,N-diethylaminomethyl group,N-propylaminomethyl group, N,N-dipropylaminomethyl group,N-methyl-N-ethylaminomethyl group, N-methylaminoethyl group,N,N-dimethylaminoethyl group, N-ethylaminoethyl group,N,N-diethylaminoethyl group, N-propylaminoethyl group,N,N-dipropylaminoethyl group, N-methyl-N-ethylaminoethyl group,N-methylaminopropyl group, N,N-dimethyaminopropyl group,N-ethylaminopropyl group, N,N-diethylaminopropyl group,N-propylaminopropyl group, N,N-dipropylaminopropyl group andN-ethyl-N-butylaminopropyl group;

hydroxyalkyl groups such as hydroxyethyl group;

alkylcarbonyloxyalkyl groups such as methylcarbonyloxyethyl group;

alkoxycarbonylalkyl groups such as methoxycarbonylmethyl group,ethoxycarbonylmethyl group, propoxycarbonylmethyl group,butoxycarbonylmethyl group, pentyloxycarbonylmethyl group andhexyloxycarbonylmehtyl group;

aryl oxycarbonylalkyl groups such as phenoxycarbonylmethyl group;

aralkyl groups such as benzyl group and phenetyl group.

In the formula (1), an unsubstituted or substituted aryl group is notlimited in particular, and includes;

aryl groups substituted by a linear, branched or cyclic alkyl group suchas phenyl group, naphtyl group, anthranyl group, 2-methylphenyl group,3-methylphenyl group, 4-methylphenyl group, 2,3-dimethylphenyl group,2,4-dimethylphenyl group, 2,5-dimethyphenyl group, 2,6-dimethylphenylgroup, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group,3,6-dimethylphenyl group, 2,3,4-trimethylphenyl group,2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group,2,4,5-trimethylphenyl group, 2,4,6-trimethylphenyl group,3,4,5-trimethyphenyl group, 2-ethylphenyl group, propylphenyl group,butylphenyl group, hexylphenyl group, cyclohexylphenyl group,octylphenyl group, 2-methyl-1-naphthyl group, 3-methyl-1-naphtyl group,4-methyl-naphtyl group, 5-methyl-1-naphtyl group, 6-methyl-1-naphtylgroup, 7-methyl-1-naphtyl group, 8-methyl-1-naphtyl group,1-methyl-2-naphthyl group, 3-methyl-2-naphthyl group,4-methyl-2-naphthyl group, 5-methyl-2-naphthyl group,6-methyl-2-naphthyl group, 7-methyl-2-naphthyl group,8-methyl-2-naphthyl group and 2-ethyl-1-naphtyl group;

aryl groups substituted a linear, branched or cyclic alkoxy group suchas 3-methoxyphenyl group, 4-methoxyphenyl group, 2,3-dimethoxyphenylgroup, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group,2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group,3,5-dimethoxyphenyl group, 3,6-dimethoxyphenyl group,2,3,4-trimethoxyphenyl group, 2,3,5-trimethoxyphenyl group,2,3,6-trimethoxyphenyl group, 2,4,5-trimethoxyphenyl group,2,4,6-trimethoxyphenyl group, 3,4,5-trimethoxyphenyl group,2-ethoxyphenyl group, propoxyphenyl group, butoxyphenyl group,hexyloxyphenyl group, cyclohexyloxyphenyl group, octyloxyphenyl group,2-methoxy-1-naphthyl group, 3-methoxy-1-naphtyl group,4-methoxy-1-naphtyl group, 5-methoxy-1-naphtyl group,6-methoxy-1-naphtyl group, 7-methoxy-1-naphtyl group,8-methoxy-1-naphtyl group, 1-methoxy-2-naphtyl group,3-methoxy-2-naphtyl group, 4-methoxy-2-naphtyl group,5-methoxy-2-naphtyl group, 6-methoxy-2-naphtyl group,7-methoxy-2-naphtyl group, 8-methoxy-2-naphtyl group and 2-ethoxy1-naphtyl group;

aryl groups substituted by halogen atom such as chlorophenyl group,dichlorophenyl group, trichlorophenyl group, bromophenyl group,dibromophenyl group, iodophenyl group, fluorophenyl group,difluorophenyl group, trifluorophenyl group, tetrafluorophenyl group andpentafluorophenyl, group;

N-monoamino substituted aryl groups or N,N-diamino substituted arylgroups such as N,N-dimethylaminophenyl group, N,N-diethylaminophenylgroup, N-phenyl-N-methylaminophenyl group, N-triyl-N-ethylaminophenylgroup, N-chlorophenyl-N-cyclohexylaminophenyl group andN,N-ditriylaminophenyl group; and alkylthioaryl group; and

arylthioaryl groups such as methylthiophenyl group, ethylthiophenylgroup, methylthionaphtyl group and phenylthiophenyl group.

In these groups, a hydrogen atom, n-propyl group, iso-propyl group,n-butyl group, iso-butyl group, n-hexyl group, n-octyl group,2-ethylhexyl group, methoxyethyl group, ethoxyethyl group, butoxyethylgroup and methoxyethoxyethyl group are preferably as the substituent ofR₁ to R₃ in particular.

Quinophthalone compounds used preferably in the aqueous ink for ink-jetrecording of the present invention are the compounds which, in theformula (1), R₁ is a hydrogen atom or an unsubstituted or substitutedalkyl group having 5 or less carbon atoms, and one of R₂ and R₃ is ahydrogen atom and the other is —CONR₄R₅ or —COOR₆ (in which each of R₄to R₆ independently, represents a hydrogen atom, an unsubstituted orsubstituted alkyl group, or an unsubstituted or substituted aryl group),and more preferably R₁ is a hydrogen atom or an unsubstituted orsubstituted alkyl group having 5 or less carbon atoms, and R₂ is ahydrogen atom, R₃ is —CONR₄R₅ (in which each of R₄ and R₆ independently,represents an unsubstituted or substituted alkyl group having 6 or morecarbon atoms, or an unsubstituted or substituted aryl group).

These compounds are especially useful as coloring matter for ink-jetrecording ink.

Specific examples of a quinophthalone compound represented by theformula (1) are shown in Table 1. In the present invention, however, thecoloring matters shown in Table 1 are not critical.

TABLE 1 Formula (1) No. R₁ R₂ R₃ 1 —C₃H₇(i) H —CON[CH₂CH(C₂H₅)C₄H₉]₂ 2—C₃H₇(i) H —CON(C₈H₁₇)₂ 3 —C₃H₇(i) H —COO(C₂H₄O)₄H 4 —C₆H₁₂(cyclo) H—COOC₈H₁₇ 5 —C₄H₉(n) H —COOC₂H₄OC₂H₄OC₄H₉ 6 —C₄H₉(i) H —CON(C₆H₁₃)₂ 7—C₈H₁₇(n) H —COOCH₂CH(C₂H₅)C₄H₉ 8 —C₁₂H₂₅(n) H —CONHC₁₈H₃₇ 9 H—CON(C₈H₁₇)₂ H 10 H —COOC₁₂H₂₅ H 11 —C₃H₇(i) —CON[CH₂CH(C₂H₅)C₄H₉]₂ H 12H —CON(C₄H₉)₂ —CON(C₄H₉)₂ 13 H —COOC₁₈H₃₇ —COOC₁₈H₃₇ 14 H —C₄H₉(n)—CON(C₄H₉)₂ 15 H —C₄H₉(n) —COOC₂H₄OC₂H₄OC₄H₉ 16 —CH₃ —COOCH₂CH(C₂H₅)C₄H₉—COOC₂H₄OC₂H₄OC₂H₅ 17 H —CON[CH₂CH(C₂H₅)C₄H₉]₂ —COOC₁₈H₃₇ 18 H—CON(CH₃)CH₂CH(C₂H₅)C₄H₉ —CON(CH₃)CH₂CH(C₂H₅)C₄H₉ 19 H —CON(C₆H₁₃)₂—CON(C₆H₁₃)₂ 20 —CH₃ —COOC₁₈H₃₇ —COOC₁₈H₃₇ 21 —CH₃ —CON(C₆H₁₃)₂—CON(C₆H₁₃)₂ 22 H —C₃H₇(i) —CON(CH₂CH₂OOCCH₃)₂ 23 —C₂H₅ —COOC₁₂H₂₅ H 24—C₄H₉(n) H —COOC₆H₄-m-N(C₂H₅)₂ 25 —C₄H₉(n) H —COOC₆H₄-m-N(C₄H₉)₂ 26—C₄H₉(n) H —COOC₆H₄-p-N(C₂H₅)₂ 27 H H —CON[CH₂CH(C₂H₅)C₄H₉]₂ 28 —C₃H₇(i)H —CON[C₈H₁₇(i)]₂ 29 —C₃H₇(i) H —CON[C₁₂H₂₅(n)]₂ 30 —C₃H₇(i) H—CON[C₁₀H₂₁(n)]₂ 31 —C₃H₇(i) H —CON[C₆H₁₃(n)]₂ 32 —C₃H₇(i) H—CON[CH₂CH(CH₃)C₅H₁₁]₂ 33 —C₃H₇(i) H —CON[CH(CH₃)C₆H₁₃]₂ 34 —C₂H₅ HCON[CH₂CH(C₂H₅)C₄H₉]₂ 35 —C₆H₁₃(n) H —CON[CH₂CH(C₂H₅)C₄H₉]₂

On the other hand, in pyridone azo compound represented by the formula(2),

each of R₇ to R₁₁ independently, represents, a hydrogen atom, a halogenatom, an unsubstituted or substituted alkyl group, an aralkyl group, anunsubstituted or substituted alkoxy group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted aryloxy group, ahydroxyl group, —NR₁₄, R₁₅ (in which each of R₁₄ and R₁₅ independently,represents a hydrogen atom, an unsubstituted or substituted alkyl group,or an unsubstituted or substituted aralkyl group), —COX₁ [in which X₁represents an unsubstituted or substituted alkoxy group, anunsubstituted or substituted aryloxy group, or —NR₁₆R₁₇ (in which eachof R₁₆ and R₁₇ independently, represents a hydrogen group, anunsubstituted or substituted alkyl group, an aralkyl group, or anunsubstituted or substituted aryl group)], —COO(CH₂)_(n)—COX₂, —OCOX₃,or —NHCOX₄ (in which each of X₂ to X₄ independently, represents anunsubstituted or substituted alkyl group, an aralkyl group, anunsubstituted or substituted aryl group, an unsubstituted or substitutedalkoxy group, or an unsubstituted or substituted aryloxy group, and n isan integer of 1 to 3),

R₁₂ represents an unsubstituted or substituted alkyl group,

R₁₃ represents an unsubstituted or substituted alkyl group, an aralkylgroup or an unsubstituted or substituted aryl group.

In the formula (2), an unsubstituted or substituted alkyl group is notlimited in particular and includes, for example, linear, branched orcyclic alkyl groups such as methyl group, ethyl group, n-propyl group,iso-propyl group, n-butyl group, iso-butyl group, tert-butyl group,n-pentyl group, iso-pentyl group, n-hexyl group, iso-hexyl group,2-ethylhexyl group, 3,5,5-trimethylhexyl group, n-heptyl group, n-octylgroup, tert-octyl group, n-nonyl group and iso-nonyl group;

cycloalkyl groups such as cyclopentyl group and cyclohexyl group;

halogeno-alkyl groups such as trifluoromethyl group and chloroethylgroup;

cyanoalkyl group such as cyanoethyl group;

alkoxyalkyl group such as methoxymethyl group, ethoxymethyl group,methoxyethyl group, ethoxyethyl group, n-propoxyethyl group,iso-propoxyethyl group, n-butoxyethyl group, iso-butoxyethyl group andtert-butoxy ethyl group.

In the formula (2), an aralkyl group is not limited in particular, andincludes, for example, aralkyl groups such as benzyl group and phenetylgroup.

In the formula (2), an unsubstituted or substituted alkoxy group is notlimited in particular, and includes, for example, linear, branched orcyclic alkoxy groups such as methoxy group, ethoxy group, n-propoxygroup, isopropoxy group, n-butoxy group, iso-butoxy group, tert-butoxygroup, n-pentyloxy group, iso-pentyloxy group, n-hexyloxy group,iso-hexyloxy group, 2-ethylhexyloxy group, 3,5,5-trimethylhexyloxygroup, n-heptyloxy group, n-octyloxy group and n-nonyloxy group;

cycloalkyl groups such as cyclopentyloxy group and cyclohexyloxy group;

alkoxyalkoxy groups such as methoxymethoxy group, ethoxymethoxy group,ethoxyethoxy group, n-propoxymethoxy group, iso-propoxymethoxy group,n-propoxyethoxy group, iso-propoxyethoxy group, n-butoxyethoxy group,iso-butoxyethoxy group, tert-butoxyethoxy group, n-pentyloxyethoxygroup, iso-pentyloxyethoxy group, n-hexyloxyethocy group,iso-hexyloxyethoxy group, 2-ethylhexyloxyethoxy group,3,5,5-trimethylhexyloxyethoxy group, n-heptyloxyethoxy group,n-octyloxyethoxy group and n-nonyloxyethoxy group;

aralkyloxy groups such as benzyloxy group.

Further, in the formula (2), an unsubstituted or substituted aryl groupis not limited in particular and includes, for example, phenyl group,toluyl group, xylyl group, naphthyl group, chlorophenyl group,bromophenyl group, fluorophenyl group and trifluoromethylphenyl group.

Further more, in the formula (2), an unsubstituted or substitutedaryloxy group is not limited in paticular and includes, for example,phenoxy group, methylphenoxy group, dimethylphenoxy group,methoxyphenoxy group, chlorophenoxy group, bromophenoxy group,fluorophenoxy group, trifluorophenoxy group and naphtyloxy group.

Especially, pyridone azo compounds used preferably in the aqueous inkfor ink-jet recording of the present invention are the compounds inwhich in the formula (2), at least one of R₇ to R₉ is —CONR₁₆R₁₇ having17 or more carbon atoms, and R₁₃ is a linear or branched alkyl grouphaving 8 or more carbon atoms, or —(CH₂)_(n)COOR₁₈ having 8 or morecarbon atoms.

More preferably, R₁₂ is a linear or branched alkyl group having 4 ormore carbon atoms, and R₁₃ is a lenear or branched alkyl group having 10or more carbon atoms.

Further more preferably, R₁₃ is a linear or branched alkyl group having14 or more carbon atoms.

Particular examples of pyridone azo compounds represented by the formula(2) are shown in Table 2, however, the compounds used in the presentinvention are not limited by these compounds.

TABLE 2 Coloring Formula (2) No. R₇ R₈ R₉ R₁₀ R₁₁ R₁₂ R₁₃ 36 H H—C₈H₁₇(n) H H —CH₃ —C₈H₁₇(n) 37 H H —C₄H₉(n) H H —CH₃ —C₈H₁₉(i) 38 H H—C₄H₉(i) H H —CH₃ —C₈H₁₇(n) 39 H H —C₄H₉(t) H H —CH₃ -ph 40 H H—C₆H₁₃(n) H H —CH₃ —CH₃-ph 41 H H cyclohexyl H H —CH₃ cyclohexyl 42 H H—OC₈H₁₇(n) H H —CH₃ —C₈H₁₇(n) 43 H H —OC₂H₅ H H —CH₃ —C₁₀H₂₁(n) 44 H Hcyclohexyloxy H H —CH₃ —C₁₀H₂₁(n) 45 H H —COOC₂H₄COOC₄H₉(n) H H —CH8—CH₂CH(C₂H₅)C₄H₉(n) 46 H H —COOCH₂COOC₄H₉(i) H H —CH₃—CH₂CH(C₂H₅)C₄H₉(n) 47 H H —COOCH₂COOC₅H₁₁(i) H H —CH₃—CH₂CH(C₂H₅)C₄H₉(n) 48 H H —COOCH₂COOC₆H₁₃(i) H H —CH₃—CH₂CH(C₂H₅)C₄H₉(n) 49 H H —COOCH₂COOC₈H₁₇(i) H H —CH₃ —C₈H₁₇(n) 50 H H—COOCH₂COOC₂H₅ H H —CH₃ —C₈H₁₇(n) 51 H H —COOC₄H₉(n) H H —CH₃ —C₈H₁₇(n)52 H H —COOC₄H₉(i) H H —CH₃ —C₈H₁₇(n) 53 H H —COOC₅H₁₁(i) H H —CH₃—CH₂CH(C₂H₅)C₄H₉(n) 54 H H —COOC₆H₁₃(i) H H —CH₃ —CH₂CH(C₂H₅)C₄H₉(n) 55H H —COOC₈H₁₇(i) H H —CH₃ —CH₂CH₂OCH(CH₃)₂ 56 H H —COOCH₂CH(C₂H₅)C₄H₉(n)H H —CH₃ —CH₂CH(C₂H₅)C₄H₉(n) 57 H H —COOCH₂COOCH₂CH(C₂H₅)C₄H₉(n) H H—CH₃ —CH₂CH(C₂H₅)C₄H₉(n) 58 H H —COOCH₂CH₂CH(CH₃)CH₂C(CH₃)₃ H H —CH₃—CH₂CH(C₂H₅)C₄H₉(n) 59 H H —COOCH₂-ph H H —CH₃ —C₁₀H₂₁(n) 60 H H—OCOCH₂CH(C₂H₅)C₄H₉(n) H H —CH₃ —C₁₀H₂₁(n) 61 H H—OCOCH₂CH₂CH(CH₃)CH₂C(CH₃)₃ H H —CH₃ —C₁₀H₂₁(n) 62 H H —OCOC₄H₉(i) H H—CH₃ —C₁₀H₂₁(n) 63 H H —OCOC₈H₁₇(n) H H —CH₃ —C₁₀H₂₁(n) 64 H H—CONHCH₂CH(C₂H₅)C₄H₉(n) H H —CH₃ —C₁₂H₂₅(n) 65 H H —CONHC₈H₁₇(n) H H—CH₃ —C₁₂H₂₅(n) 66 H H —CONHCH₂CH₂CH(CH₃)CH₂C(CH₃)₃ H H —CH₃ —C₁₂H₂₅(n)67 H H —CON[CH₂CH(C₂H₃)C₄H₉(n)]₂ H H —CH₃ —CH₂CH(C₂H₅)C₄H₉(n) 68 H H—CON[C₄H₉(n)]₂ H H —CH₃ —C₁₂H₂₅(n) 69 H H —CON[C₄H₉(i)]₂ H H —CH₃—C₁₂H₂₅(n) 70 H H —CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —CH₃ —C₈H₁₇(n) 71 H H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —CF₃ —CH₂CH(C₂H₅)C₄H₉(n) 72 H H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —C₂H₅ —CH₂CH(C₂H₅)C₄H₉(n) 73 H H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —CH₃ —CH₂-ph 74 H H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —CH₃ —CH₂CH₂CH₂OCH(CH₃)₂ 75 H H—CON[C₈H₁₇(n)]₂ H H —CH₃ —C₈H₁₇(n) 76 H —CF₃ H H H —CH₃ —C₉H₁₉(i) 77 H—CF₃ H H H —CH₃ —C₉H₁₉(n) 78 H —OC₄H₉(i) F H H —CH₃ —C₈H₁₇(n) 79 H —C₂H₅—C₂H₅ H H —CH₃ —C₁₀H₂₁(n) 80 H —OCH₃ —OCH₃ H H —CH₃ —C₁₀H₂₁(n) 81 —C₂H₅H H H H —CH₃ —C₁₀H₂₁(n) 82 H —OCOCH₂CH(C₂H₅)C₄H₉(n) H H H —CH₃ —C₈H₁₇(n)83 H —OCOC₂H₄CH(CH₃)CH₂C(CH₃)₃ H H H —CH₃ —CH₂CH₂OCH(CH₃)₂ 84 H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H —CH₃ —C₈H₁₇(n) 85 H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H —CH₃ —CH₂CH(C₂H₅)C₄H₉(n) 86 —C₄H₉(i) H HH H —CH₃ —C₈H₁₇(n) 87 —OC₄H₉(i) H H H H —CH₃ —C₈H₁₇(n) 88—COOCH₂COOC₈H₁₇(n) H H H H —CH₃ —C₈H₁₇(n) 89 —COOC₅H₁₁(i) H H H H —CH₃—CH₂CH(C₂H₅)C₄H₉(n) 90 —OCOCH₂CH(C₂H₅)C₄H₉(n) H H H H —CH₃—CH₂CH(C₂H₅)C₄H₉(n) 91 —OCOC₂H₄CH(CH₃)CH₂C(CH₃)₃ H H H H —CH₃—CH₂CH(C₂H₅)C₄H₉(n) 92 —CONHCH₂CH(C₂H₅)C₄H₉(n) H H H H —CH₃ —C₈H₁₇(n) 93—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H H —CH₃ —C₈H₁₇(n) 94—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H H —CH₃ —CH₂CH(C₂H₅)C₄H₉(n) 95—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H H —CH₃ —CH₂CH₂OCH(CH₃)₂ 96 —C₃H₇(i) H HH —C₃H₇(i) —CH₃ —CH₂CH(C₂H₅)C₄H₉(n) 97 —CH₃ H H H —C₃H₇(i) —CH₃—CH₂CH(C₂H₅)C₄H₉(n) 98 —C₄H₉(t) H H —C₄H₉(t) H —CH₃ —CH₂CH(C₂H₅)C₄H₉(n)99 —C₃H₇(i) H H H H —CH₃ —CH₂CH(C₂H₅)C₄H₉(n) 100 H —C₃H₇(i) H H H —CH₃—CH₂CH(C₂H₅)C₄H₉(n) 101 H cyclhexyl H H H —CH₃ —C₈H₁₇(n) 102 H—OC₈H₁₇(n) H H H —CH₃ —C₈H₁₇(n) 103 H —COOCH₈COOC₄H₉(i) H H H —CH₃—CH₂CH(C₂H₅)C₄H₉(n) 104 H —COOC₄H₉(i) H H H —CH₃ —C₈H₁₇(n) 105 H—COOCH₂COOCH₂CH(C₂H₅)C₄H₉(n) H H H —CH₃ —CH₂CH(C₂H₅)C₄H₉(n) 106 H—OCOC₈H₁₇(n) H H H —CH₃ —C₁₀H₂₁(n) 107 H —CONHCH₂CH(C₂H₅)C₄H₉(n) H H H—CH₃ —C₁₂H₂₅(n) 108 H —CONHC₈H₁₇(n) H H H —CH₃ —C₁₂H₂₅(n) 109 H—CON[C₄H₉(i)]₂ H H H —CH₃ —C₁₂H₂₅(n) 110 H —CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H HH —C₂H₅ —CH₂CH(C₂H₅)C₄H₉(n) 111 H —CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H —CH₃—CH₂-ph 112 H —CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H —CH₃ —CH₂CH₂CH₂OCH(CH₃)₂113 H —CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H —CH₃ —C₁₃H₂₇(n) 114 H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H —CH₃ —C₁₄H₂₉(n) 115 H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H —CH₃ —C₁₆H₃₃(n) 116 H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H —CH₃ —C₁₈H₃₇(n) 117 H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H —C₃H₇(n) —C₈H₁₇(n) 118 H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H —C₄H₉(n) —C₈H₁₇(n) 119 H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H —C₄H₉(n) —C₁₄H₂₉(n) 120 H—CON[C₁₄H₂₉(n)]₂ H H H —CH₃ —C₈H₁₇(n) 121 —CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H HH H —CH₃ —C₁₃H₂₇(n) 122 —CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H H —CH₃—C₁₄H₂₉(n) 123 —CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H H —CH₃ —C₁₆H₃₃(n) 124—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H H —C₃H₇(n) —C₈H₁₇(n) 125—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H H —C₄H₉(n) —C₈H₁₇(n) 126—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H H —C₄H₉(n) —C₁₂H₂₅(n) 127—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H H —C₄H₉(n) —C₁₄H₂₉(n) 128 H H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —C₃H₇(n) —C₈H₁₇(n) 129 H H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —C₄H₉(n) —C₈H₁₇(n) 130 H H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —C₆H₁₃(n) —C₈H₁₇(n) 131 H —CON[C₁₄H₂₉(n)]₂—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —C₄H₉(n) —C₈H₁₇(n) 132 H —CON[C₁₄H₂₉(n)]₂—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —CH₃ —C₁₄H₂₉(n) 133 H H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —CH₃ —C₁₃H₂₇(n) 134 H H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —CH₃ —C₁₄H₂₉(n) 135 H H—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H —CH₃ —C₁₆H₃₃(n) 136—CON[CH₂CH(C₂H₅)C₄H₉(n)]₂ H H H H —C₆H₁₃(n) —C₈H₁₇(n) 137 H H—COOCH₂CH(C₂H₅)C₄H₉(n) H H —C₄H₉(n) —C₈H₁₇(n) 138 H H —C₈H₁₇(n) H H —CH₃—CH₂COOC₆H₁₈(n) 139 H H —C₄H₉(n) H H —CH₃ —CH₂COOC₈H₁₇(n) 140 H H—C₄H₉(i) H H —CH₃ —CH₂COOC₈H₁₇(n) 141 H H —C₄H₉(t) H H —CH₃—CH₂COOC₈H₁₇(n) 142 H H —C₆H₁₃(n) H H —CH₃ —CH₂COOC₈H₁₇(n) 143 H HCyclohexyl H H —CH₃ —CH₂COOC₆H₁₁(cyclo) 144 H H —OC₈H₁₇(n) H H —CH₃—CH₂COOC₁₀H₂₁(n) 145 H H cyclohexyloxy H H —CH₃ —CH₂COOC₁₀H₂₁(n) 146 H H—COOCH₂COOC₄H₉(i) H H —CH₃ —CH₂COOCH₂CH(C₂H₅)C₄H₉ 147 H H—COOCH₂COOC₅H₁₁(i) H H —CH₃ —CH₂COOCH₂-ph 148 H H —COOCH₂COOC₆H₁₃(n) H H—CH₃ —CH₂CONHC₈H₁₇(n) 149 H H —COOCH₂COOC₈H₁₇(n) H H —CH₃—CH₂COOC₈H₁₇(n) 150 H H —COOCH₂COOC₂H₅ H H —CH₃—CH₂CON[CH₂CH(C₂H₅)C₄H₉]₂ 151 H H —COOC₄H₉(i) H H —CH₃ —CH₂COOC₈H₁₇(n)152 H H —COOC₅H₁₁(i) H H —CH₃ —CH₂CO—(3-methylphenoxy) 153 H H—COOC₆H₁₃(n) H H —CH₃ —CH₂CO—[4-(t-butyl)phenoxy] 154 H H —COOC₈H₁₇(n) HH —CH₃ —CH₂CO—(2,5-dimethylphenoxy) 155 H H —COOCH₂CH(C₂H₅)C₄H₉ H H —CH₃—C₂H₄COOC₄H₉(i) 156 H H —COOCH₂COOCH₂CH(C₂H₅)C₄H₉ H H —CH₃—CH₂COOCH₂CH(C₂H₅)C₄H₉ 157 H H —COOC₂H₄CH(CH₃)CH₂C(CH₃)₃ H H —CH₃—CH₂COOC₈H₁₇(n) 158 H H —COOCH₂-ph H H —CH₃ —CH₂COOCH₂-ph 159 H H—OCOCH₂CH(C₂H₅)C₄H₉ H H —CH₃ —CH₂COOC₈H₁₇(n) 160 H H—OCOC₂H₄CH(CH₃)CH₂C(CH₃)₃ H H —CH₃ —C₂H₄COOC₄H₉(i) 161 H H —OCOC₄H₉(i) HH —CH₃ —CH₂COOC₈H₁₇(n) 162 H H —OCOC₈H₁₇(n) H H —CH₃ —CH₂COOC₁₀H₂₁(n)163 H H —CONHCH₂CH(C₂H₅)C₄H₉ H H —CH₃ —CH₂CON[CH₂CH(C₂H₅)C₄H₉]₂ 164 H H—CONHC₈H₁₇(n) H H —CH₃ —CH₂CONHC₈H₁₇(n) 165 H H—CONHC₂H₄CH(CH₃)CH₂C(CH₃)₃ H H —CH₃ —CH₂COOCH₂CH(C₂H₅)C₄H₉ 166 —C₃H₇(i)H H H —C₃H₇(i) —CH₃ —CH₂COOCH₂CH(C₂H₅)C₄H₉ 167 —CH₃ H H H —C₃H₇(i) —CH₃—CH₂COOCH₂CH(C₂H₅)C₄H₉ 168 —C₄H₉(t) H H —C₄H₉(t) H —CH₃ —CH₂COOC₈H₁₇(n)169 —C₃H₇(i) H H H H —CH₃ —CH₂COOC₈H₁₇(n) 170 H —C₃H₇(i) H H H —CH₃—CH₂COOC₈H₁₇(n) 171 H H —CONHCH₂CH(C₂H₅)C₄H₉ H H —CH₃—C₂H₄COOCH₂CH(C₂H₅)C₄H₉ 172 H H —CONHCH₂CH(C₂H₅)C₄H₉ H H —CH₃—C₂H₄CON[CH₂CH(C₂H₅)C₄H₉]₂ 173 H H —CONHCH₂CH(C₂H₅)C₄H₉ H H —CF₃—CH₂COOCH₂CH(C₂H₅)C₄H₉ 174 H H —CONHCH₂CH(C₂H₅)C₄H₉ H H —C₄H₉(n)—CH₂COOCH₂CH(C₂H₅)C₄H₉ 175 H —CF₃ H H H —CH₃ —CH₂COOC₆H₁₃(n) 176 H —CF₃H H H —CH₃ —C₂H₄COOC₈H₁₇(n) 177 H —OC₄H₉(i) F H H —CH₃ —CH₂COOC₈H₁₇(n)178 H —C₂H₅ —C₂H₅ H H —CH₃ —CH₂COOC₈H₁₇(n) 179 H —OCH₃ —OCH₃ H H —CH₃—CH₂COOC₈H₁₇(n) 180 —C₂H₅ H H H —C₂H₅ —CH₃ —C₂H₄CON[CH₂CH(C₂H₅)C₄H₉]₂181 H —OCOCH₂CH(C₂H₅)C₄H₉ H H H —CH₃ —CH₂COOC₈H₁₇(n) 182 H—OCOC₂H₄CH(CH₃)CH₂C(CH₃)₃ H H H —CH₃ —CH₂COOC₁₀H₂₁(n) 183 H—COOCH₂CH(C₂H₅)C₄H₉ H H H —CH₃ —CH₂COOCH₂CH(C₂H₅)C₄H₉ 184 H—COOCH₂COOCH₂CH(C₂H₅)C₄H₉ H H H —CF₃ —CH₂COOCH₂CH(C₂H₅)C₄H₉ 185 —C₄H₉(i)H H H H —CH₃ —CH₂COOCH₂CH(C₂H₅)C₄H₉ 186 —OC₄H₉(i) H H H H —CH₃—CH₂COOCH₂CH(C₂H₅)C₄H₉ 187 —COOCH₂COOC₈H₁₇(n) H H H H —CH₃—CH₂COOCH₂CH(C₂H₅)C₄H₉ 188 —COOC₅H₁₁(i) H H H H —CH₃ —CH₂COOC₈H₁₇(n) 189—OCOCH₂CH(C₂H₅)C₄H₉ H H H H —CH₃ —CH₂COOC₈H₁₇(n) 190—OCOC₂H₄CH(CH₃)CH₂C(CH₃)₃ H H H H —CH₃ —CH₂COOC₈H₁₇(n) 191—COOCH₂CH(C₂H₅)C₄H₉ H H H H —CH₃ —C₂H₄CON[CH₂CH(C₂H₅)C₄H₉]₂ 192—COOCH₂COOCH₂CH(C₂H₅)C₄H₉ H H H H —CH₃ —CH₂COOCH₂CH(C₂H₅)C₄H₉ 193—CONHCH₂CH(C₂H₅)C₄H₉ H H H H —CH₃ —CH₂CONHCH₂CH(C₂H₅)C₄H₉ 194—COOCH₂COOC₂H₄OCH(CH₃)₂ H H H H —CH₃ —CH₂COOC₂H₄OCH(CH₃)₂

The quinophthalone compounds represented by the formula (1) which areused in ink for ink-jet recording of the present invention are producedby conventionally known methods, for example, the processes disclosed inJapanese Patent Laid-Open Hei 39269/1993 and Japanese Patent Laid-OpenHei 292264/1995, etc. For example, these compounds can be prepared bythe process comprising reacting 3-hydroxy-2-methyl-4-cinchonic acidderivatives represented by the formula (3) and phthalic anhydridederivatives represented by the formula (4).

wherein R₁ to R₃ are the same as defined above.

The reaction between the compounds represented by the formula (3) andthe compounds represented by the formula (4) is carried out at 150 to230° C. for 1 to 20 hours in the presence of a high boiling solvent suchas nitrobenzene, sulphorane, dichlorobenzene, N-methyl-2-pirrolidone and1,3-dimethyl-2-imidazolidinone.

The compounds which R₁ to R₃ in the quinophthalone compound representedby the formula (1) is —CONR₄R₅ or —COOR₆ can be prepared by reacting thecompounds of the formula (3) having the above substituents and thecompounds represented by the formula (4) having the above substituents.The compounds also can be prepared by reacting the compounds representedby the formula (3) having carboxyl group and the compounds representedby the formula (4), and successively carrying out esterification oramidation.

The compounds in which R₁ to R₃ are alkylthio groups can be prepared bydirectly substituting with the alkyl thiol in the presence of an alkalifrom the compounds of the formula (1).

The compounds can also be prepared by reacting the compounds previouslyhalogenated R₁ to R₃ in compounds of the formulas (3) and (4), andsuccessively substituting the halogen with the alkyl thiol in thepresence of an alkali. A process for preparing the compounds representedby the formula (1), however, is not limited by the above process.

The compounds represented by the formula (2) and used for ink forink-jet recording of the present invention, for example, can be preparedby coupling the anilines represented by the formula (5) and pyridonesrepresented by the formula (6) according to a conventionally knowncoupling method.

wherin R₇ to R₁₃ are the same as above.

Specifically, the compounds represented by the formula (2) are obtained,for example, by adding sodium nitrite aqueous solution to anilinesrepresented by the formula (5) in hydrochloric acid, and successivelyadding the resulting diazo compounds to pyridones represented by theformula (6) for azo coupling reaction, and separating the thus-obtainedproduct through filtration. A process for preparing the compoundsrepresented by the formula (2), however, is not limited by the aboveprocess.

The compounds of the present invention are useful in various kind ofink, especially as a yellow hue coloring matter for ink-jet recordingsystem. The coloring matter can be used as such. However, when it isused in the ink-jet recording system in particular, it may be purifiedby desalting treatment, for example, with an ion exchange resin orthrough ultrafiltration, or by column chromatography in order to preventclogging of a jet nozzle in a recording apparatus owing to impurities orinorganic materials contained in the coloring matter.

The ink for ink-jet recording of the present invention contains at leastone yellow hue coloring matter selected from the group consisting of aquinophthalone compound represented by the formula (1) and a pyridoneazo compound represented by the formula (2), water and a resin as maincomponents, namely, as essential components, and, if necessary, furtherother components, for example, additives such as a dispersant and anemulsifying agent and auxiliaries. It takes the form of an emulsion bydispersing the resin fine particles colored with the coloring matter ofthe present invention in an aqueous medium and emulsifying thedispersion.

The ink for ink-jet recording of the present invention may contain anorganic solvent and additives as required. The coloring mattersrepresented by the formula (1) and the formula (2) may be used eithersingly or in combination, or may be mixed with other coloring mattershaving a different structure.

In the ink for ink-jet recording of the present invention, the resinconstituting the resin fine particles can be a resin having an ionicgroup on the surface. For example, various resins such as a polyesterresin, a vinyl polymer, a styrenic resin, a styrene-acrylic copolymerand a polyurethane resin are available.

(a) The polyester resin comprises polycarboxylic acids and polyhydricalcohols. A resin obtained by the polymerization of one or morepolycarboxylic acids and one or more polyhydric alcohols is mentioned.

Polycarboxylic acids are not particularly limited. Examples thereofinclude aromatic polycarboxylic acids, aromatic oxycarboxylic acids,aliphatic dicarboxylic acids and alicyclic dicarboxylic acids such asterephthalic acid, isophthalic acid, o-phthalic acid,1,5-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid,diphenic acid, sulfoterephthalic acid, 5-sulfoisophthalic acid,4-sulfophthalic acid, 4-sulphonaphthalene-2,7-dicarboxylic acid,5-[4-sulfophenoxy]isophthalic acid, sulphoterephtalic acid, p-oxybenzoicacid, p-(hydroxyethoxy)benzoic acid, succinic acid, adipic acid, azelaicacid, sebacic acid, dodecanedicarboxylic acid, fumaric acid, maleicacid, itaconic acid, hexahydrophthalic acid, tetrahydrophthalic acid,trimellitic acid, trimesic acid and pyromellitic acid. These can also beused as metal salts and ammonium salts.

The polyhydric alcohols are not particularly limited. Examples thereofinclude aliphatic polyhydric alcohols, alicyclic polyhydric alcohols andaromatic polyhydric alcohols such as ethylene glycol, propylene glycol,1,3-propanediol, 2,3-butanediol, 1,4-butanediol, 1,5-pentanediol,1,6-hexanediol, neopentyl glycol, diethylene glycol, dipropylene glycol,2,2,4-trimethyl-1,3-pentanediol, polyethylene glycol, polypropyleneglycol, polytetramethylene glycol, trimethylolethane,trimethylolpropane, glycerin, pentaerythritol, 1,4-cyclohexanediol,1,4-cyclohexanedimethanol, spiroglycol, tricyclodecanediol,tricyclodecanedimethanol, m-xylene glycol, o-xylene glycol,1,4-phenylene glycol, bisphenol A and lactone-type polyester polyols.

With respect to the polyester resin obtained by polymerizing one or moreof the polycarboxylic acids and one or more of the polyhydric alcohols,a resin in which a polar group in the end of the high-molecular chain isblocked with a known compound capable of blocking an end is alsoavailable.

(b) The vinyl polymer, the styrenic resin and the styrene-acryliccopolymer are not particularly limited. For example, those obtained fromthe following polymerizable monomers are mentioned.

Examples of the polymerizable monomers include vinyl aromatichydrocarbons such as styrene, o-methylstyrene, m-methylstyrene,p-methylstyrene, α-methylstyrene, p-ethylstyrene, 2,4-dimethylstyrene,p-tert-butylstyrene, p-chlorostyrene and divinylbenzene; (meth)acrylicacid esters such as methyl acrylate, ethyl acrylate, butyl acrylate,n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutylacrylate, tert-butyl acrylate, n-pentyl acrylate, isopentyl acrylate,neopentyl acrylate, 3-(methyl)butyl acrylate, 2-ethylhexyl acrylate,cyclohexyl acrylate, hexyl acrylate, octyl acrylate, nonyl acrylate,decyl acrylate, undecyl acrylate, dodecyl acrylate, phenyl acrylate,methyl methacrylate, n-propyl methacrylate, isopropyl methacrylate,n-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate,n-pentyl methacrylate, isopentyl methacrylate, neopentyl methacrylate,3-(methyl)butyl methacrylate, 2-ethylhexyl methacrylate, hexylmethacrylate, octyl methacrylate, nonyl methacrylate, decylmethacrylate, undecyl methacrylate and dodecyl methacrylate; unsaturatedcarboxylic acids such as acrylic acid, methacrylic acid, itaconic acidand maleic acid; (meth)acrylamide; n-substituted maleimide; maleicanhydride; (meth)acrylonitrile; vinyl ketone; vinyl acetate; andvinylidene chloride. Resins obtained by polymerizing one or more ofthese monomers are mentioned.

(c) The polyurethane resin comprises isocyanates and compounds with afunctional group capable of reacting with isocyanates. A resin obtainedby polymerizing one or more of the isocyanates and one or more of thecompounds is mentioned.

Examples of the isocyanates include:

aliphatic polyisocyanates such as ethylene diisocyanate, trimethylenediisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate,octamethylene diisocyanate, nonamethylene diisocyanate,2,2-dimethylpentane diisocyanate, 2,2,4-trimethylhexamethylenediisocyanate, decamethylene diisocyanate, butenediisocyanate,1,3-butadiene-1,4-diisocyanate, 2,4,4-trimethylhexamethylenediisocyanate, 1,6,11-undecatriisocyanate, 1,3,6-hexamethylenetriisocyanate, 1,8-diisocyanato-4-isocyanatomethyloctane,2,5,7-trimethyl-1,8-diisocyanato-5-isocyanatomethyloctane,bis(isocyanatoethyl) carbonate, bis(isocyanatoethyl) ether, 1,4-butyleneglycol dipropyl ether-ω,ω′-diisocyanate, lysine diisocyanatomethylester, lysine triisocyanate,2-isocyanatoethyl-2,6-diisocyanatoethyl-2,6-diisocyanatohexanoate,2-isocyanatopropyl-2,6-diisocyanatohexanoate, xylylene diisocyanate,bis(isocyanatoethyl)benzene, bis(isocyanatopropyl)benzene,α,α,α′,α′-tetramethylxylylene diisocyanate, bis(isocyanatobutyl)benzene,bis(isocyanatomethyl)naphthalene, bis(isocyanatomethyl)diphenyl ether,bis(isocyanatoethyl) phthalate, mesitylene triisocyanate and2,6-di(isocyanatomethyl)furan;

alicyclic polyisocyanates such as isophorone diisocyanate,bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane diisocyanate,cyclohexane diisocyanate, methylcyclohexane diisocyanate,dicyclohexyldimethylmethane diisocyanate,2,2-dimethyldicyclohexylmethane diisocyanate,bis(4-isocyanato-n-butylidene) pentaerythritol, dimer acid diisocyanate,2-isocyanatomethyl-3-(3-isocyanatopropyl)-5-isocyanatomethylbicyclo[2,2,1]-heptane,2-isocyanatomethyl-3-(3-isocyanatopropyl)-6-isocyanatomethylbicyclo[2,2,1]heptane,2-isocyanatomethyl-2-(3-isocyanatopropyl)-5-isocyanatomethylbicyclo[2,2,1]heptane,2-isocyanatomethyl-2-(3-isocyanatopropyl)-6-isocyanatomethylbicyclo[2,2,1]heptane,2-isocyanatomethyl-3-(3-isocyanatopropyl)-6-(2-isocyanatoethyl)bicyclo[2,2,1]heptane,2-isocyanatomethyl-3-(3-isocyanatopropyl)-6-(2-isocyanatoethyl)bicyclo[2,1,1]heptane,2-isocyanatomethyl-2-(3-isocyanatopropyl)-5-(2-isocyanatoethyl)bicyclo[2,1,1]heptane,2-isocyanatomethyl-2-(3-isocyanatopropyl)-6-(2-isocyanatoethyl)bicyclo[2,2,1]heptaneand norbornanebis(isocyanatomethyl);

aromatic polyisocyanates such as phenylene diisocyanate, tolylenediisocyanate, ethylphenylene diisocyanate, isopropylenephenylenediisocyanate, dimethylphenylene diisocyanate, diethylphenylenediisocyanate, diisopropylphenylene diisocyanate, trimethylbenzenetriisocyanate, benzene triisocyanate, naphthalene diisocyanate,methylnaphthalene diisocyanate, biphenyl diisocyanate, tolidinediisocyanate, 4,4′-diphenylmethane diisocyanate,3,3′-dimethyldiphenylmethane-4,4′-diisocyanate,bibenzyl-4,4′-diisocyanate, bis(isocyanatophenyl)ethylene,3,3′-dimethoxybiphenyl-4,4′-diisocyanate, triphenylmethanetriisocyanate, polymeric MDI, naphthalene triisocyanate,diphenylmethane-2,4,4′-triisocyanate,3-methyldiphenylmethane-4,6,4′-triisocyanate,4-methyldiphenylmethane-3,5,2′,4′,6′-pentaisocyanate,phenylisocyanatomethyl isocyanate, phenylisocyanatoethylethylisocyanate, tetrahydronaphthylene diisocyanate, hexahydrobenzenediisocyanate, hexahydrodiphenylmethane-4,4′-diisocyanate, diphenyl etherdiisocyanate, ethylene glycol diphenyl ether diisocyanate, 1,3-propyleneglycol diphenyl ether diisocyanate, benzophenone diisocyanate,diethylene glycol diphenyl ether diisocyanate, dibenzofurandiisocyanate, carbazole diisocyanate, ethylcarbazole diisocyanate anddichlorocarbazole diisocyanate;

sulfur-containing aliphatic isocyanates such as thiodiethyldiisocyanate, thiopropyl diisocyanate, thiodihexyl diisocyanate,dimethylsulfone diisocyanate, dithiodimethyl diisocyanate, dithiodiethyldiisocyanate, dithiopropyl diisocyanate anddicyclohexylsulfide-4,4′-diisocyanate;

aromatic sulfide-type isocyanates such asdiphenylsulfide-2,4′-diisocyanate, diphenylsulfide-4,4′-diisocyanate,3,3′-dimethoxy-4,4′-diisocyanatodibenzyl thioether,bis(4-isocyanatomethylbenzene) sulfide and4,4′-methoxybenzenethioethyleneglycol-3,3′-diisocyanate;

aromatic disulfide-type isocyanates such asdiphenyldisulfide-4,4′-diisocyanate,2,2′-dimethyldiphenyldisulfide-5,5′-diisocyanate,3,3′-dimethyldiphenyldisulfide-5,5′-diisocyanate,3,3′-dimethyldiphenyldisulfide-6,6′-diisocyanate,4,4′-dimethyldiphenyldisulfide-5,5′-diisocyanate,3,3′-dimethoxydiphenyldisulfide-4,4′-diisocyanate and4,4′-dimethoxydiphenyldisulfide-3,3′-diisocyanate;

aromatic sulfone-type isocyanates such asdiphenylsulfone-4,4′-diisocyanate, diphenylsulfone-3,3′-diisocyanate,benzidinesulfone-4,4′-diisocyanate,diphenylmethanesulfone-4,4′-diisocyanate,4-methyldiphenylmethanesulfone-2,4′-diisocyanate,4,4′-dimethoxydiphenylsulfone-3,3′-diisocyanate,3,3′-dimethoxy-4,4′-diisocyanatodibenzylsulfone,4,4′-dimethyldiphenylsulfone-3,3′-diisocyanate,4,4′-di-tert-butyldiphenylsulfone-3,3′-diisocyanate,4,4′-methoxybenzeneethylenedisulfone-3,3′-diisocyanate and4,4′-dichlorodiphenylsulfone-3,3′-diisocyanate;

sulfonic acid ester-type isocyanates such as4-methyl-3-isocyanatobenzenesulfonyl-4′-isocyanatophenol ester and4-methoxy-3-isocyanatobenzenesulfonyl-4′-isocyanatophenol ester;

aromatic sulfonic acid amides such as 4-methyl-4′-isocyanate,dibenzenesulfonylethylenediamine-4,4′-diisocyanate,4,4′-methoxybenzenesulfonylethylenediamine-3,3′-diisocyanate and4-methyl-3-isocyanatobenzenesulfonylanilide-4-methyl-3′-isocyanate; and

sulfur-containing heterocyclic compounds such asthiophene-2,5-diisocyanate, thiophene-2,5-diisocyanatomethyl,1,4-dithian-2,5-diisocyanate and 1,4-dithian-2,5-diisocyanatomethyl.

Examples of the compounds with a functional group capable of reactingwith the isocyanates include:

polyol compounds: aliphatic polyols such as ethylene glycol, diethyleneglycol, triethylene glycol, tetraethylene glycol, propylene glycol,dipropylene glycol, butylene glycol, neopentyl glycol, glycerin,trimethylolethane, trimethylolpropane, butanetriol, 1,2-methylglycoside,pentaerythritol, dipentaerythritol, tripentaerythritol, sorbitol,erythritol, threitol, ribitol, arabinitol, xylitol, allitol, mannitol,dolucitol, iditol, glycol, inositol, hexanetriol, triglycerol,diglycerol, polyethylene glycol, polypropylene glycol, polytetraethyleneether glycol, tris(2-hydroxyethyl) isocyanurate, cyclobutanediol,cyclopentanediol, cyclohexanediol, cycloheptanediol, cyclooctanediol,cyclohexanedimethanol, hydroxypropylcyclohexanol,tricyclo[5,2,1,0,^(2,6)]decanedimethanol, bicyclo[4,3,0]nonanediol,dicyclohexanediol, tricyclo[5,3,1,1]dodecanediol,bicyclo[4,3,0]nonanedimethanol, tricyclo[5,3,1,1]dodecane-ethanol,hydroxypropyltricyclo[5,3,1,1]dodecanol, spiro[3,4]octanediol,1,1′-bicyclohexylidenediol, cyclohexanetriol, maltitol and lactitol;

aromatic polyols such as dihydroxynaphthalene, trihydroxynaphthalene,tetrahydroxynaphthalene, dihydroxybenzene, benzenetriol,biphenyltetraol, pyrogallol, (hydroxynaphthyl)pyrogallol,trihydroxyphenanthrene, bisphenol A, bisphenol F, xylylene glycol,di(2-hydroxyethoxy)benzene, bisphenol A-bis(2-hydroxyethyl ether),tetrabromobisphenol A, tetrabromobisphenol A-bis(2-hydroxyethyl ether)and bisphenol S;

halogenated polyols such as dibromoneopentyl glycol, polyester polyols,polycaprolactones, polythioether polyols, polyacetal polyols,polycarbonate polyols, polycaprolactone polyols, polythioether polyols,polybutadiene polyols, furandimethanol, condensation reaction productsof organic acids such as oxalic acid, glutamic acid, adipic acid, aceticacid, phthalic acid, isophthalic acid, salicylic acid and pyromelliticacid and the polyols, addition reaction products of the polyols andalkylene oxides such as ethylene oxide and propylene oxide, additionreaction products of alkylene polyamines and alkylene oxides,2,2-dimethylollactic acid, 2,2-dimethylolpropionic acid,2,2-dimethylolbutanoic acid, 2,2-dimethylolvaleric acid,3,4-diaminobutanesulfonic acid, 3,6-diamino-2-toluenesulfonic acid andtheir caprolactone modified products;

2-mercaptoethanol, 3-mercapto-1,2-propanediol, glycerindi(mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane,2,4-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol,1,3-dimercapto-2-propanol, 2,3-dimercapto-1,3-butanediol,pentaerythritol tris(3-mercaptopropionate), pentaerythritolmono(3mercaptopropionate), pentaerythritol tris(thioglycolate),pentaerythritol pentakis(3-mercaptopropionate),hydroxymethyltris(mercaptoethylthiomethyl)methane,1-hydroxyethylthio-3-mercaptoethylthiobenzene,4-hydroxy-4′-mercaptodiphenylsulfone, 2-(2-mercaptoethylthio)ethanol,dihydroxyethylsulfide mono(3-mercaptopropionate), dimercaptoethanemono(salicylate) andhydroxyethylthiomethyltris(mercaptoethylthio)methane.

Further, polyamino compounds such as ethylenediamine,diethylenetriamine, triethylenetetramine, propylenediamine,butylenediamine, hexamethylenediamine, cyclohexylenediamine, piperazine,2-methylpiperazine, phenylenediamine, tolylenediamine, xylylenediamine,α,α′-methylenebis(2-chloroaniline)-3,3′-dichloro-α,α′-biphenylamine,m-xylenediamine, isophoronediamine, N-methyl-3,3′-diaminopropylamine andnorbornenediamine;

polythiol compounds, α-amino acids such as serine, lysine and histidine;and halo-substituted products of these active hydrogen compounds canalso be used. These may be used either singly or in combination.

These resins can also be used either singly or in combination, but theyare not critical at all.

The resin containing the ionic group on the surface exhibits theexcellent water dispersibility.

Examples of the ionic group include a sulfonic acid group, a carboxylicacid group, a sulfuric acid group, a phosphoric acid group, a phosphonicacid group, a phosphinic acid group, alkali metal salt groups orammonium salt groups thereof, and primary to tertiary amine groups. Acarboxylic acid alkali metal salt group, a carboxylic acid ammonium saltgroup, a sulfonic acid alkali metal salt group and a sulfonic acidammonium salt group are preferable. A sulfonic acid alkali metal saltgroup and a sulfonic acid ammonium salt group are especially preferablein view of the water dispersion stability. The introduction of the ionicgroup can be conducted by adding a monomer having an ionic group in theformation of the resin.

For example, when a carboxylic acid alkali metal salt group or acarboxylic acid ammonium salt group is introduced into a polyester resinas an ionic group, a method can be employed in which a polycarboxylicacid such as trimellitic acid is introduced into a system at theterminal stage of the polymerization of a polyester to add a carboxylgroup to an end of a resin, and this group is further neutralized withammonia or sodium hydroxide to convert the same into a carboxylic acidsalt group.

Moreover, when a sulfonic acid alkali metal salt group or a sulfonicacid ammonium salt group is introduced into polyester resin fineparticles as an ionic group, a mono- or di-carboxylic acid having asulfonic acid alkali metal salt group or a sulfonic acid ammonium saltgroup can be introduced into a system to introduce this ionic group intothe polyester resin.

As the salt, an ammonium ion, Li, Na, K, Mg, Ca, Cu and Fe arementioned. K and Na are especially preferable.

The present invention includes the resin fine particles colored with atleast one coloring matter selected from the group consisting of acompound represented by formula (1) and a compound represented by theformula (2), the dispersion obtained by dispersing the resin fineparticles in the aqueous medium, and the ink for ink jet recording whichis the emulsion resulting from the emulsification through thedispersion.

The resin fine particles colored with the coloring matter of the presentinvention can be produced by the following methods.

1. Method in which the coloring matter is dissolved or dispersed in thepolymerizable monomer, and emulsion polymerization is then conducted.

2. Method in which after a resin is obtained by polymerization of thepolymerizable monomer, the coloring matter is directly added thereto,and additives are further added as required to uniformly dissolve ordisperse the same for coloration.

3. Method in which a material obtained by dissolving or dispersing thecoloring matter in a water-soluble organic solvent (for example,acetone, methyl ethyl ketone, tetrahydrofuran or dioxane) or an ordinaryfilm-forming aid (such as texanol or N,N-dimethylpyrrolidone) is addedto the resin obtained by the polymerization, additives are added asrequired, and these are uniformly dissolved or dispersed for coloration.

4. Method in which a material obtained by dissolving or dispersing thecoloring matter in a water-insoluble organic solvent (for example,toluene) is added to the resin obtained by the polymerization, additivesare added as required, and these are uniformly dissolved or dispersed,and water is further added to form a water dispersion and conductemulsification, and the water-insoluble organic solvent is thendistilled off as required for coloration.

5. Method in which after obtaining the water dispersion of the resin,coloration is conducted by a high-temperature dying method in which thecoloring matter for ink jet recording is added thereto and the mixtureis treated at a high temperature.

With respect to the resin fine particles colored with the coloringmatter which are produced by these methods, the particle diameter is notparticularly limited. In the dispersion obtained by dispersing the samein an aqueous medium using a dispersing agent, the smaller particlediameter is preferred. When the particles are used as the dispersion ofthe coloring matter for ink jet recording, the average particle diameteris between 0.01 and 1 μm, preferably between 0.05 and 0.8 μm. Further,the production of the dispersion obtained by dispersing the resin fineparticles colored with the coloring matter in the aqueous medium is notparticularly limited. A dispersion having a desired composition can beobtained using a dispersing agent selected according to the applicationof the dispersion.

In the colored resin fine particles, the coloring matter is influencedby the compatibility of the coloring matter with the resin, and itincludes a coloring matter which is uniformly dissolved in the resin anda coloring matter which is partially uniformly dispersed in or adheredto the surface of the resin. A coloring matter which is uniformlydissolved in the resin is preferable. The amount of the coloring matterrelative to the resin is usually between 1 and 90% by weight, preferablybetween 5 and 50% by weight. However, it is not particularly limited.

The colored resin fine particles or the dispersion thereof can be usedas various coloring and recording materials upon making the most of thehydrophobic nature thereof. Further, the ink for ink jet recording canbe produced as an emulsion by emulsifying the same.

The ink for ink jet recording of the invention is an emulsion in whichthe coloring matter represented by formula (1) and/or the coloringmatter represented by the formula (2) (hereinafter, simply refer as“coloring matter for ink-jet recording”), the resin and water are usedas essential components, and it can be produced by the followingmethods.

1. Method in which after the coloring matter for ink jet recording isdissolved or dispersed in the polymerizable monomer, the emulsionpolymerization is conducted, additives are added thereto as required,these are uniformly dissolved or dispersed, and water is further addedto form a water dispersion and conduct emulsification.

2. Method in which after a resin is obtained by polymerization, thecoloring matter for ink jet recording is directly added thereto,additives are added as required to uniformly dissolve or disperse thesame, and water is further added to form a water dispersion and conductemulsification.

3. Method in which a material obtained by dissolving or dispersing thecoloring matter for ink jet recording in a water-soluble organic solvent(for example, acetone, methyl ethyl ketone, tetrahydrofuran or dioxane)or an ordinary film-forming aid (such as texanol orN,N-dimethylpyrrolidone) is added to the resin obtained by thepolymerization, additives are added thereto as required, these areuniformly dissolved or dispersed, water is further added to form a waterdispersion and conduct emulsification, and the water-soluble organicsolvent is then distilled off as required.

4. Method in which a material obtained by dissolving or dispersing thecoloring matter for ink jet recording in a water-insoluble organicsolvent (for example, toluene) is added to the resin obtained by thepolymerization, additives are added thereto as required, these areuniformly dissolved or dispersed, water is further added to form a waterdispersion and conduct emulsification, and the water-insoluble organicsolvent is then distilled off as required.

5. Method in which after obtaining the water dispersion of the resin,the resin is colored by a high-temperature dying method in which thecoloring matter for ink jet recording is added thereto and the mixtureis treated at a high temperature, and the water dispersion of thecolored resin fine particles is emulsified.

In the production, filtration with a microporous filter such as amembrane filter is sometimes conducted to remove insoluble matters.

With respect to the colored resin fine particles in the water dispersionobtained by emulsification (“the resin fine particles colored with thecoloring matter” is sometimes simply referred to as “the colored resinfine particles”), the average particle diameter is preferably between0.01 and 1 μm, more preferably between 0.05 and 0.8 μm. When the averageparticle diameter is too small, there is a possibility of decreasing theimage density or the water resistance. When it is too large, there is apossibility that the dispersion stability in ink is decreased to form aprecipitate, as a results, the storage stability is decreased, or thatclogging of a nozzle occurs.

The amount of the coloring matter in the colored resin fine particlesdepends on the use, the aim, the types of the coloring matter, the inkcomposition, the printing density of the ink and the clogging property.The amount of the coloring matter in the resin is between 1 and 90% byweight, preferably between 5 and 50% by weight.

When the amount of the coloring matter is small, a large amount of inkis required to obtain a satisfactory recorded image, exerting a load ona printing head of a recording device or recording paper. When it islarge, the coloring matter tends to be precipitated from the resinparticles to form a precipitate in the ink, inducing the clogging of theprinting head.

The ink for ink-jet recording of the present invention (hereinaftersimply referred as “ink”) may contain, for adjusting the color tone ofthe ink, other coloring matters, and known dyes or pigments treated inthe form of an emulsion or a fine dispersion so as not to impair inkcharacteristics.

The amount of the colored resin fine particles in the ink is between 1and 70% by weight, preferably between 5 and 50% by weight.

The ink of the invention can contain a water-soluble organic solvent, asrequired, for adjusting the wettability, the surface tension, theviscosity and the drying rate of the ink.

Examples of the water-soluble organic solvent include polyhydricalcohols such as ethylene glycol, diethylene glycol, triethylene glycol,polyethylene glycol, propylene glycol, polypropylene glycol,1,3-propanediol, glycerin and thioglycol; polyhydric alcohol ethers suchas ethylene glycol monoethyl ether, ethylene glycol monobutyl ether,diethylene glycol monobutyl ether, dipropylene glycol monoethyl etherand triethylene glycol monomethyl ether; ketones such as acetone andmethyl ethyl ketone; amides such as N,N-dimethylformamide,N,N-diethylformamide and N,N-dimethylacetamide; nitrogen-containingcompounds such as 2-pyrrolidone, N-methyl-2-pyrrolidone,N-vinyl-2-pyrrolidone and 1,3-dimethyl-2-imidazolidinone; ethers such astetrahydrofuran and dioxane; alcohols such as methanol, ethanol,1-propanol, 2-propanol, 1-butanol and 2-butanol; and glycerin. When thewater-soluble organic solvent is used, it is advisable that the amountthereof is between 1 and 20% by weight based on the total amount of theink.

In order to improve the storage stability of the ink, it is advisable toadjust pH to between 7 and 10. Examples of a pH adjustor include NaHCO₃,Na₂B₄O₇, alkanolamines such as ethanolamine, diethanolamine andtriethanolamine, and alkali metal hydroxides such as potassium hydroxideand lithium hydroxide.

The ink of the present invention can contain, as required, variousadditives used so far. Examples of the additives include an ultravioletabsorber, an antioxidant, a dispersing agent, a dispersion stabilizer, achelating agent, a water-soluble polymer, a masking agent, arustproofing agent, an antiseptic, a viscosity modifier, a surfactant, asurface-tension modifier, a pH adjustor, a specific resistance modifier,a near infrared absorber and a penetrant.

The ink of the present invention comprising the components can be usedas the ink for ink jet recording system and also as ink for writing ormarking instrument. It is excellent in the recording characteristics,the storage stability, the fixability to the recording medium, thevividness of the recorded image, the light resistance and the waterresistance.

Since the coloring matter used in the invention has the high solubilityin the organic solvent, it can also be used in solvent-type jet ink fortextile printing or printing.

EXAMPLE

The invention is illustrated more specifically by referring to thefollowing Examples. However, the invention is not limited thereto.Incidentally, “parts” in Examples are on the weight basis.

Coloring Matter Production Example 1

Coloring matter No. 1 in Table 1 was produced by the following process.

285 Parts of sulfolane was added to 21.1 parts of trimellitic anhydride,and the solution was heated to 185° C. Further, 24.6 parts of3-hydroxy-2-methyl-6-isopropylquinoline-4-carboxylic acid was added tothe solution, and reacted at 200° C. for 1 hour.

37.2 Parts of the compound of the formula (7) which is the precursor ofthe desired product was obtained.

5 Parts of the compound of the formula (7) was added to 25 parts ofo-dichlorobenzene, the mixture was heated at 100° C. 3.6 Parts ofthionyl chloride was added dropwise to the mixture and maintained at thetemperature for 2.5 hours and excess thionyl chloride was distilled offunder reduced pressure. Further, 15 parts of di(2-ethylhexyl)amine wasadded dropwise at 100° C. and maintained at the temperature whilestirring for 2 hours and then was cooled to room temperature.

The resulting reaction mixture was discharged in 50 parts of methanol toobtain 6 parts of the coloring matter No. 1 represented by the formula(8);

Maximum absorption wavelength (λmax) of the coloring matter in

toluene was 453 nm and 429 nm, and gram absorptibity coefficient (εg) in453 nm was 90600 ml/g cm. The elemental analysis values of the compoundwere shown below.

Elemental analysis C H N found (%) 76.3 8.4 4.6 calculated (%) 76.2 8.44.7

The compound had high solvent solubility, and had 30% or more solubilityin toluene at room temperature.

Coloring Matter Production Example 2

The coloring matter of No. 118 in the table 2 was prepared as below.

26.7 Parts of m-nitrobenzoyl chloride was added to 100 parts of tolueneand further 34.8 parts of di-2-ethylhexylamine and 11.4 parts ofpyridine and then reacted for four hours. Subsequently, the reactionmixtures were filtered and removed precipitated solid by filtration, andthen 56.2 parts of the compound represented by the formula (9),

which is the precursor of the desired compound, was obtained byconcentration of the filtrate.

53.0 Parts of the compound of the formula (9) was added to 250 parts ofdimethylformamide and further 100 parts of 20% aqueous solution ofsodium hydrosulfide was added and reacted at 70° C. for 2 hours, andthen the reaction mixture was cooled to 30° C. The reaction mixture wasdischarged in 250 parts of water and was added to 100 parts of toluene.After mixing and standing the mixture, the upper layer was extracted andconcentrated to obtain 46.5 parts of the compound represented by theformula (10) which is the precursor of the desired product.

39.6 Parts of n-octyl amine and 17.0 parts of cyano ethyl acetate weremixed and reacted for 2 hours. Subsequently, 30 parts of water and 29.8parts of 3-oxysoenanto acid ethyl was charged to the mixture and reactedat 90° C. for 2 hours. The reaction mass was discharged in 400 parts of3% aqueous solution of sulfuric acid, and further 100 parts of toluenewas added, after mixing and standing, upper layer was extracted andconcentrated to obtain 40.8 parts of the compound represented by theformula (11), precursor of the desired product;

14.3 Parts of the compound of the formula (10) and 29 parts of 11%aqueous solution of hydrochloric acid was added to 100 parts ofmethanol, and was cooled to 10° C. or less while stirring. Subsequently,11 parts of 30% aqueous solution of sodium nitrite was added and reactedfor 1 hour, and further 0.18 parts of sulfamic acid was added andstirred at 10° C. or less for 30 minutes (solution of diazonium salt).On the other hand, 100 parts of methanol, 12.1 parts of the compound ofthe formula (11) and 30 parts of 6% aqueous solution of sodium hydroxidewere mixed and then were cooled to 10° C. or less.

The above solution of diazonium salt was added to the mixture andreacted for 3 hours. After charging 500 parts of water to the mixtureand stirring. The supernatant was removed by decantation and only tarconstituent was taken out. Purification of the constituent was carriedout with column chromatography to obtain 12.7 parts of the coloringmatter of No 118 represented by the formula (12);

Maximum absorption wavelength (λmax) of the coloring matter in toluenewas 432 nm, and gram absorptibity coefficient (εg) in 432 nm was 62000ml/g cm. The elemental analysis values of the compound were shown below.

Elemental analysis C H N found (%) 72.6 9.5 10.5 calculated (%) 72.8 9.610.4

The compound had high solvent solubility, and had 30% or more solubilityin toluene at room temperature.

Example 1

Production Example of Colored Resin Fine Particles and a Dispersion (A)Thereof

To an autoclave equipped with a thermometer and a stirrer, 180 parts ofdimethyl terephthalate, 10 parts of pentasodium sulfoisophthalic aciddimethyl ester, 130 parts of ethylene glycol, 25 parts oftricyclodecanedimethanol and 0.1 part of tetrabutoxytitanate wascharged, and the mixture was heated at 180 to 220° C. for approximately3 hours for transesterification. Subsequently, the reaction mixture washeated to 240° C., the pressure in the autoclave was then lowered slowlyto 10 mmHg, and the reaction was continued for 1 hour. The pressure inthe autoclave was returned to atmospheric pressure to obtain acopolyester resin.

Then, 100 parts of the resulting polyester resin, 150 parts of methylethyl ketone, 150 parts of tetrahydrofuran and 10 parts of the coloringmatter for ink-jet recording indicated at No. 1 in Table 1 were mixed.Thereafter, 600 parts of deionized water was added thereto, and thesewere further mixed. This mixture was filtered through a 0.8-micronmembrane filter, and heated to distill off the solvent. After cooling,deionized water was added to adjust the solid content to 20% by weight.Thus, a dispersion (A) of colored resin fine particles was obtained. Theresin fine particles dispersed in the dispersion were fine particles ofthe resin colored in yellow tint, having an average particle diameter of0.2 μm.

Evaluation of characteristics:

Glycerin and deionized water were added to the dispersion of the coloredresin fine particles to obtain aqueous ink having a solid content of 15%by weight.

This aqueous ink was charged into an ink cartridge for a piezo-type inkjet printer, and printing and image recording were conducted with thisprinter. The tests were conducted with respect to the following items.The results are shown in Table 2.

The evaluation standards of the test items are described below.

(A) Evaluation of an Emulsion:

The condition of the emulsion in production of the emulsion ink wasvisually evaluated.

Evaluation Standard:

The condition of the emulsion is good. ⊚ A floating matter is slightlyobserved, which is not actually ∘ problematic though. Gelation isslightly observed, which seems likely to be Δ problematic. The conditionof the emulsion is bad, and it is problematic as ink. ×

(B) Evaluation of an Image:

An image was formed on plain paper, and a blotted condition was visuallyevaluated.

Evaluation Standard:

No blotting is observed. ⊚ Blotting is observed without any influence onan image. ∘ Blotting is notably observed. ×

(C) Evaluation of an Image Recording Density:

The plain paper having the recorded image was measured for the recordingdensity (OD value) using a reflection densitometer (manufactured byMacbeth) to evaluate the image recording density.

Evaluation Standard:

The OD value is 1.1 or more. ⊚ The OD value is 1.0 to less than 1.1. ∘The OD value is 0.8 to less than 1.0 Δ The OD value is less than 0.8. ×

(D) Evaluation of a Water Resistance:

With respect to the printed portion of the plain paper having therecorded image for test, the printing density (OD value) before dippingin water or after dipping in water and air-drying was measured with areflection densitometer. The water resistance was evaluated uponcomparing OD₁.

OD₁=(OD value after dipping in water and air-drying)/(OD value beforedipping in water)×100

Evaluation Standard:

OD₁ is 90 to 100%. ⊚ ⊚ OD₁ is 80 to less than 90%. ⊚ OD₁ is 70 to lessthan 80%. ∘ OD₁ is 50 to less than 70%. Δ OD₁ is less than 50%. ×

(E) Evaluation of a Light Resistance:

A printing density (OD value) before irradiation or after 100 hours ofirradiation was measured using a xenon fadeometer (manufactured by SugaShikenki), and the light resistance was evaluated upon comparing OD₂.

OD₂=(OD value after irradiation)/(OD value before irradiation)×100

Evaluation Standard:

OD₂ is 90 to 100%. ⊚ ⊚ OD₂ is 80 to less than 90%. ⊚ OD₂ is 70 to lessthan 80%. ∘ OD₂ is 50 to less than 70%. Δ OD₂ is less than 50%. ×

(F) Evaluation of a Storage Stability of Ink:

In order to evaluate the initial storage stability of aqueous ink(storage at 40° for 1 month) and the long-term storage stability thereof(storage at 40° C. for 3 months), the conditions of the aqueous inkafter these storages were visually observed. Further, the recording wasconducted continuously with the printer for a long period of time, andthe clogging was observed.

(F-1) Conditions After Storage of the Ink:

Evaluation Standard:

No problem without any precipitate or any floating matter. ∘ A floatingmatter is slightly observed. Δ Problematic with a precipitate and afloating matter observed. ×

(F-2) Clogging:

Evaluation Standard:

Normal ∘ Negligible level at the present stage Δ Abnormal ×

Example 2

Production Example of a Dispersion (B) of Colored Resin Fine Particles

To an autoclave equipped with a thermometer and a stirrer, 150 parts ofdimethyl terephthalate, 50 parts of dimethyl isophthalate, 5 parts ofpentasodium sulfoisophthalic acid dimethyl ester, 150 parts of ethyleneglycol, 250 parts of neopentyl glycol and 0.1 part oftetrabutoxytitanate, and the mixture was heated at 180 to 220° C. forapproximately 3 hours for transesterification. Subsequently, thereaction mixture was heated to 240° C., the pressure in the autoclavewas then lowered slowly to 10 mmHg, and the reaction was continued for 1hour. The pressure in the autoclave was returned to atmospheric pressureto obtain a copolyester resin. Then, 100 parts of the resultingpolyester resin, 150 parts of methyl ethyl ketone, 150 parts oftetrahydrofuran and 10 parts of the coloring matter for ink-jetrecording indicated at No. 5 in Table 1 were mixed. Thereafter, 600parts of deionized water was added thereto, and these were furthermixed. This mixture was filtered through a 0.8 micron membrane filter,and heated to distill off the solvent. After cooling, deionized waterwas added to adjust the solid content to 20% by weight. Thus, adispersion (B) of colored resin fine particles was obtained. The resinfine particles dispersed in the dispersion were fine particles of theresin colored in yellow tint, having an average particle diameter of 0.3μm.

Glycerin and deionized water were added to the dispersion of the coloredresin fine particles to obtain aqueous ink having a solid content of 15%by weight. The ink characteristics were evaluated as in Example 1, andthe results are shown in Table 3.

Examples 3 to 151

Ink was produced by the process of Example 1 or 2 using the coloringmatters for ink jet recording shown in Tables 1 or 2, and the inkcharacteristics were evaluated. The results are shown in Table 3.Incidentally, “Ink production process” in Table 3 refers to the processof Example 1 or 2.

All the aqueous inks using the coloring matters for ink jet recording ofthe invention were especially excellent in the water-resistance and alsoexcellent in the long-term storage stability. Further, the recordedimage was good without blotting, and excellent in the light resistance.

Comparative Example 1

Ink was produced as in Example 2 using quinophthalone-based coloringmatter represented by the formula (13);

Partially insoluble matter was observed. The ink was passed through thefilter to remove the insoluble matter, and the characteristics thereofwere then evaluated as in Example 1. Consequently, as shown in Table 3,the coloring matter was quite worse than the coloring matters for inkjet recording of the invention.

Comparative Example 2

Ink was produced as in Example 1 using the quinophthalone compoundrepresented by the formula (14);

Since the solubility of the coloring matter was low, an insoluble matterwas observed. The ink was passed through the filter to remove theinsoluble matter, and the characteristics thereof were then evaluated asin Example 1.

Consequently, as shown in Table 3, the coloring matter was quite worsethan the coloring matters for ink jet recording of the invention.

Comparative Example 3

Ink was produced as in Example 1 using oil soluble dyestuff C.I. SolventYellow 16;

Since the solubility of the coloring matter was low, an insoluble matterwas observed. The ink was passed through the filter to remove theinsoluble matter, and the characteristics thereof were then evaluated asin Example 1.

Consequently, as shown in Table 3, the coloring matter was quite worsethan the coloring matters for ink jet recording of the invention.

TABLE 3 preparation Evaluation of characteristics Coloring process F-1F-1 F-2 F-2 Example No. of ink A B C D E (after 1 month) (after 3 month)(after 1 month) (after 3 month) 1 1 Example 1 ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 2 5Example 2 ◯ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 3 2 Example 1 ◯ ⊚ ◯ ⊚ ⊚⊚ ◯ Δ ◯ Δ 4 3 ↑ ◯ ⊚ Δ⊚ ⊚ ◯ Δ ◯ Δ 5 4 ↑ Δ ⊚ X ⊚ ⊚ ◯ X ◯ X 6 6 ↑ ◯ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 7 9 ↑ ◯ ⊚ ◯⊚ ⊚ ◯ Δ ◯ Δ 8 12 ↑ ⊚ ⊚ ◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 9 13 ↑ Δ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 10 17 ↑ ⊚⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 11 19 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ ◯ ◯ ◯ 12 20 ↑ ◯ ⊚ ◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯13 21 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 14 25 ↑ Δ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 15 26 ↑ Δ ⊚ Δ ⊚ ⊚◯ Δ ◯ Δ 16 2 Example 2 ⊚ ⊚ ◯ ⊚ ⊚⊚ ◯ ◯ ◯ Δ 17 3 ↑ ◯ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 18 4↑ Δ ⊚ X ⊚ ⊚ ◯ X ◯ X 19 5 ↑ ◯ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 20 6 ↑ ◯ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 2110 ↑ Δ ⊚ X ⊚ ⊚ ◯ Δ ◯ Δ 22 11 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 23 15 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ◯ Δ 24 16 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 25 22 ↑ ◯ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 26 23 ↑ Δ ⊚ X ⊚⊚ ◯ X ◯ X 27 24 ↑ Δ ⊚ X ⊚ ⊚ ◯ X ◯ X 28 27 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 29 28Example 1 ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 30 29 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 31 30 ↑ ⊚ ⊚ ⊚⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 32 31 ↑ ◯ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 33 32 ↑ ⊚ ⊚ ◯ ⊚ ⊚⊚ ◯ ◯ ◯ ◯ 34 33↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 35 34 ↑ ⊚ ⊚ ◯ ⊚ ⊚ ◯ ◯ ◯ ◯ 38 35 ↑ ⊚ ◯ ⊚ ⊚ ⊚⊚ ◯ ◯ ◯◯ 37 36 ↑ ◯ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 38 38 Example 2 ◯ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 39 41Example 1 ◯ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 40 42 ↑ ◯ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 41 44 ↑ ◯ ⊚ Δ ⊚ ⊚◯ Δ ◯ Δ 42 46 ↑ Δ ⊚ Δ ⊚⊚ ⊚ ◯ Δ ◯ Δ 43 47 ↑ ◯ ⊚ Δ ⊚⊚ ⊚ ◯ Δ ◯ Δ 44 49 ↑ ◯⊚ Δ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 45 50 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 46 52 ↑ Δ ⊚ X ⊚ ⊚ Δ X ◯ X 4753 ↑ Δ ⊚ X ⊚ ⊚ Δ X ◯ X 48 55 ↑ Δ ⊚ X ⊚ ⊚ ◯ Δ ◯ Δ 49 56 Example 2 ◯ ⊚ ◯⊚⊚ ⊚ ◯ ◯ ◯ ◯ 50 57 ↑ ◯ ⊚ ◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 51 58 ↑ ◯ ⊚ ◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 52 60↑ ◯ ⊚ Δ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 53 61 ↑ ◯ ⊚ ◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 54 63 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯Δ 55 64 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 56 65 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ X ◯ X 57 66 Example 2 Δ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 58 69 Example 1 Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 59 70 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯◯ ◯ 60 71 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 61 72 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 62 73 ↑ ◯ ⊚ ◯⊚⊚ ⊚ ◯ ◯ ◯ ◯ 63 74 ↑ ◯ ⊚ ◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 64 75 ↑ ◯ ⊚ ◯ ⊚⊚ ⊚ ◯ Δ ◯ Δ 65 76↑ Δ ⊚ Δ ⊚ ⊚ Δ X ◯ X 66 78 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 67 79 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ X ◯ X68 81 Example 2 Δ ⊚ Δ ⊚ ⊚ ◯ X ◯ X 69 82 ↑ ⊚ ⊚ ◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 70 83 ↑ ◯ ⊚◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 71 84 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 72 85 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 7388 ↑ ◯ ⊚ ◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 74 91 ↑ ◯ ⊚ ◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 75 94 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯◯ ◯ ◯ 76 95 ↑ ◯ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 77 101 Example 1 ◯ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 78102 ↑ ◯ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 79 103 ↑ Δ ⊚ Δ ⊚⊚ ⊚ ◯ Δ ◯ Δ 80 104 ↑ Δ ⊚ X ⊚ ⊚ ◯X ◯ X 81 105 ↑ ◯ ⊚ ◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 82 106 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 83 107 ↑ Δ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 84 108 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ X ◯ X 85 109 Example 1 Δ ⊚ Δ ⊚ ⊚ ◯Δ ◯ Δ 86 110 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 87 111 ↑ ◯ ⊚ ◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 88 112 ↑ ⊚⊚ ◯ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 89 113 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 90 114 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯◯ 91 115 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 92 116 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 93 133 ↑ ⊚ ⊚⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 94 134 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 95 135 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯96 121 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 97 122 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 98 123 ↑ ⊚ ⊚ ⊚⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 99 117 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 100 118 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯101 119 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 102 124 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 103 125 ↑ ⊚ ⊚⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 104 128 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 105 129 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯◯ 106 130 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 107 131 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 108 132 ↑⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 109 120 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 110 126 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯◯ ◯ ◯ 111 127 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚⊚ ◯ ◯ ◯ ◯ 112 138 ↑ ◯ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 113 142Example 2 ◯ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 114 143 Example 1 ◯ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 115 144↑ ◯ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 116 146 ↑ ◯ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 117 148 ↑ ◯ ⊚ Δ ⊚ ⊚ ◯ Δ◯ Δ 118 149 ↑ ◯ ⊚ ◯ ⊚ ⊚ ◯ ◯ ◯ ◯ 119 151 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ X ◯ X 120 152 ↑ Δ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 121 154 ↑ ◯ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 122 155 ↑ Δ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ123 157 ↑ ◯ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ Δ 124 158 Example 2 Δ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 125 159↑ Δ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 126 160 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ X 127 162 ↑ Δ ⊚ ◯ ⊚ ⊚ ◯ Δ◯ Δ 128 163 ↑ Δ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 129 165 ↑ Δ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 130 166 ↑ Δ⊚ Δ ⊚ ⊚ ◯ X ◯ X 131 167 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ X ◯ X 132 168 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ133 171 Example 1 Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 134 172 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ X 135 173↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ X 136 174 ↑ Δ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ X 137 175 ↑ Δ ⊚ X ⊚ ⊚ ◯ X◯ X 138 176 ↑ Δ ⊚ X ⊚ ⊚ ◯ X ◯ X 139 177 ↑ ◯ ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 140 178 ↑ Δ⊚ Δ ⊚ ⊚ ◯ Δ ◯ Δ 141 180 Example 1 ◯ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 142 181 ↑ ◯ ⊚ ◯ ⊚ ⊚◯ Δ ◯ Δ 143 183 Example 2 ◯ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ 144 184 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯145 187 ↑ ⊚ ⊚ ◯ ⊚ ⊚ ◯ ◯ ◯ ◯ 146 188 ↑ ◯ ⊚ Δ ⊚ ⊚ ◯ ◯ ◯ Δ 147 189 ↑ ◯ ⊚ ◯⊚ ⊚ ◯ ◯ ◯ ◯ 148 190 ↑ ⊚ ⊚ ◯ ⊚ ⊚ ◯ ◯ ◯ ◯ 149 191 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 150192 ↑ ⊚ ⊚ ⊚ ⊚⊚ ⊚ ◯ ◯ ◯ ◯ 151 193 ↑ ◯ ⊚ ◯ ⊚ ⊚ ◯ Δ ◯ Δ Compara. Formula ↑X ◯ X ◯ ⊚ X X X X Exam. 1 (13) Compara. Formula Example 1 X ◯ X ◯ ◯ X XX X Exam. 2 (14) Compara. C.I. Solvent ↑ X ◯ X ◯ X X X X X Exam. 3Yellow 16

POSSIBILITY FOR UTILIZATION IN INDUSTRY

The coloring matter for ink-jet recording of the present invention isexcellent in water-resistance in particular, and further is excellent inlight resistance and compatibility with a resin. Ink for ink-jetrecording prepared using the coloring matter has excellent properties inlight resistance and storage stability.

The ink of the present invention, when it was used for ink-jet recordingsystem, enables formation of a high quality image without blotting, andobtained recording image has excellent characters in water-resistance

1. An aqueous ink for ink-jet recording comprising water and a resin asan emulsion, wherein the resin is colored with a pyridone azo compoundrepresented by the formula (2);

wherein each of R₇ to R₁₁ independently, represents a hydrogen atom, ahalogen atom, an unsubstituted or substituted alkyl group, an aralkylgroup, an unsubstituted or substituted alkoxy group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted aryloxy group, ahydroxyl group, —NR₁₄R₁₅ in which each of R₁₄ and R₁₅ independently,represents a hydrogen atom, an unsubstituted or substituted alkyl group,or an aralkyl group, —COX₁ in which X₁ represents an unsubstituted orsubstituted alkoxy group, an unsubstituted or substituted aryloxy group,or —NR₁₆R₁₇ in which each of R₁₆ and R₁₇ independently, represents ahydrogen atom, an unsubstituted or substituted alkyl group, an aralkylgroup, or an unsubstituted or substituted aryl group,—COO(CH₂)_(n)—COX₂, —OCOX₃, or —NHCOX₄, in which X₂ to X₄ represents anunsubstituted or substituted alkyl group, an aralkyl group, anunsubstituted or substituted aryl group, an unsubstituted or substitutedalkoxy group, or an unsubstituted or substituted aryloxy group, and n isan integer of 1 to 3, provided that at least one of R₇ to R₉ is—CONR₁₆R₁₇ having 17 or more carbon atoms, R₁₂ represents a linear orbranched alkyl group having 4 or more carbon atoms, R₁₃ represents alinear or branched alkyl group having 8 or more carbon atoms.
 2. Apyridone azo compound represented by the formula (2);

wherein each of R₇ to R₁₁ independently, represents a hydrogen atom, ahalogen atom, an unsubstituted or substituted alkyl group, an aralkylgroup, an unsubstituted or substituted alkoxy group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted aryloxy group, ahydroxyl group, —NR₁₄R₁₅ in which each of R₁₄ and R₁₅ independently,represents a hydrogen atom, an unsubstituted or substituted alkyl group,or an aralkyl group, —COX₁ in which X₁ represents an unsubstituted orsubstituted alkoxy group, an unsubstituted or substituted aryloxy group,or —NR₁₆R₁₇ in which R₁₆ and R₁₇ independently, represents a hydrogenatom, an unsubstituted or substituted alkyl group, an aralkyl group, oran unsubstituted or substituted aryl group, —COO(CH₂)_(n)—COX₂, —OCOX₃,or —NHCOX₄ in which X₂ to X₄ represents an unsubstituted or substitutedalkyl group, an aralkyl group, an unsubstituted or substituted arylgroup, an unsubstituted or substituted alkoxy group, or an unsubstitutedor substituted aryloxy group, and n is an integer of 1 to 3, providedthat at least one of R₇ to R₉ is —CONR₁₆R₁₇ having 17 or more carbonatoms, R₁₂ represents a linear or branched alkyl group having 4 or morecarbon atoms, R₁₃ represents a linear or branched alkyl group having 8or more carbon atoms.